Consumer Products – Shaowen Wu, Gregory Horn, Wild Flavors Inc

Abstract for “Genipin-rich material” and its use

The method for preparing Genipin-rich materials from Genipa Americana fruit is disclosed. It can be used as a cross-linking agent or as raw material to make colors. Genipin-rich materials are useful in many applications, including personal care, cosmetics and dietary supplements, packaging, textiles as well as food, drinks, drugs, and animal feeds.

Background for “Genipin-rich material” and its use

Today, synthetic chemicals such as colorants and cross-linking agents have a declining acceptance in the food cosmetics, animal feed, and textile industries. People prefer natural and organic ingredients in food, cosmetics, textile, biomaterial, and other products.

“Genipin can be described as a colorless compound. It is a member of the iridoid family. It is highly active chemically. It reacts instantly when mixed with compounds that have primary amine groups such as amino acids and collagen. The product can quickly turn blue, green or black if there is oxygen. Genipin, an iridoid ester, can be hydrolyzed into genipinic acids. This acid can also react with other compounds to produce red and brown colorants. Genipin colorants are stable to heat and pH. Genipin is a colorant that comes from plants. This makes it a great choice for baking and canning applications.

“Large amount of iridoids, such as geniposide, gardenoside, genipin-1-b-gentiobioside, geniposidic acid and genipin, can be found in Gardenia jasminoides Ellis fruit. Geniposide is an iridoid-related glycoside that makes up 7-8% of the fruit’s weight. However, only trace amounts are found in Gardenia fruits. The iridoids found in Gardenia fruits were traditionally extracted with methanol or alcohol, then separated on active carbon as yellow pigment, and then treated with enzymes with beta-glucosidic or proteolytic activity to transform glycoside iridoids into aglycone forms, genipinic or genipinic acids. “KR1020010096213A) – Genipinic or genipinic acids can then be combined with other compounds to make colorants.

“Genipin and other iridoid compounds, such as genipinic acid, genipin-gentiobioside, geniposide and geniposidic acid, are found also in the fruits and leaves of Genipa americana, also known as Genipap, or Huito, a tropical wild plant. Genipin can be found in mature fruits. Its quantity can range from 0 to 3.0% depending on the fruit’s ripeness. Genipin can be stored in the plant cell, but it will not become established there. Genipin reacts spontaneously with amino acids found in fruit pulp, and will change color in an environment that is either blue or black if the cell is damaged. Our previous patent application (US20090246343A1) described how to make coloring (blue-colored) fruit juice from Genipa Americana fruit pulp and juices of other fruits and vegetables. The natural acid-stable, blue juice has been widely used in the food and beverage industry. Lopes et al. (U.S. Pat. No. No. 7,927,637B2) used raw Genipa Americana fruit pulp unprocessed juice, mixed with glycine, or with glycine plus stearch, to create blue colorants. Patrice Andre (US20100196298A1) and a co-worker used coloring materials from the plant extract of Genipa Americana, Gardenia jasminoides or Rothmannia. These were bound to a solid substrate to create cosmetic compositions.

“Genipin can not only generate colorants but can also act as a cross-linking agent. Campbell et al. Campbell et al. discovered a biodegradable polymer that used genipin as a cross-linking agent (EP2093256A2). These plastics can be used in biological systems such as wound repair, implant, drug delivery and encapsulation, among other uses. Fujikawa et al. claimed (U.S. Pat. No. No. 4,983,524), the use of iridoid-aglycone (genipin) as a cross-linking agents to create immobilized enzyme beads for the food industry. R. Quijano and H. (US 20080195230A1) described the use of Genipin to fix whole, naturally occurring tissues in order to reduce immunogenicity and antigenicity, and to prevent the tissue from being enzymatically degraded when it is implanted into a host.

However, the process of producing pure genipin has been complicated in the past, with HPLC separation and a high cost. The art does not describe the method of making a stable extract from Genipa Americana. It is used as a cross-linking agent and natural colorant in food, drugs, nutritional supplements and personal care products.

The present disclosure reveals a method to produce stable, genipin rich extracts from Genipa Americana plants. This involves both aqueous and polar solvent extraction. The powder is a genipin rich extract with an off-white colour and a genipin content of about 97%.

“The present disclosure also provides applications of genipin rich extracts in natural colourant production and forming polmers for use in many areas such as food, drugs, nutritional supplement, cosmetics and animal feed. You can find examples of these uses in many patent documents, including U.S. Pat. No. No.

“All ratios and proportions are stated ‘by weight’ as they appear in this document. Except where otherwise stated. All patents, applications for patents and technical publications cited herein are also included by reference.”

The present disclosure reveals a method to produce stable genipin rich extracts from Genipa Americana plants. This involves both organic non-polar solvent and aqueous solvent extraction. The powder form of the genipin rich extract obtained is off-white and contains a genipin content of about 97%. Further, the present disclosure reveals the use of genipin rich extracts in the production natural heat-stable colorsants and as a cross-linking agent. This can be used in many areas such as food, drugs, nutritional supplements and personal care products.

“Starting Materials”

“Materials can be whole fruits, fruit pulp, juice, juice, juice concentrate, dried fruit powder, juice or fruit juice, water-insoluble parts of fruit, and Genipa americana leaves L.”

“Process for Genipin Rich Extraction”

“Next, the aqueous or concentrated genipin rich aqueous extraction may be further extracted using non-polar organic solvents. This involves suitable mixing (by shaking and agitation in a ratio of approximately 1:1). These non-polar organic solvents are polarity indexes between 0 and 5.0, with a water solubility of less than 30%. After the organic solvent phase has been separated from the aqueous phase, it can be siphoned or sucked using a high-speed centrifuge. Depending on the extraction efficiency, non-polar solvent extraction can be repeated 2 to 3 times. The genipin rich extracts can then be dried by evaporation. Organic solvents can be recycled and used for genipin extraction. The genipin-rich extract is the yellow-colored or off-white remaining solid. It contains a minimum of 70% w/w.

Geneipin-rich extracts can be either aqueous or from polar solvents. They are obtained from the raw materials described. The polar solvents are those that have water solubility of at least 100% and a polarity index greater then 5.0. These include water, acetic acids, methanol (ethanol, propanols, isopropanols, dimethyl sulfoxide), dimethyl formamide or water. While this list does not limit the solvents used, it is important to note that food safety is a consideration. Water, ethanol, iso-propanol and iso-propanol are preferred extracts for food use. Acetic, citric, and phosphate buffer solutions are preferred.

Geneipin-rich organic solvents can also be obtained from the aqueous and polar solvent extracts mentioned above. Non-polar organic solvents are those that have less than 30% water solubility and a greater polarity index of 0 to 5.0. These include ethyl and butyl alcohols, diethylethers, hexanes, 2-butanones, chloroforms, 1-butanol and methyl-t-butylethers, toluenes, carbon tetrachloride and trichloroethylene. While this list does not limit the solvents used, it is recommended that ethyl, butyl, and n?butanol be preferred due to their food safety.

Organic solvent extracts from the raw materials described may also be considered genepin-rich extracts. These organic solvents can be any with a polarity index lower than 6.0 or mixtures of them in different ratios. To obtain colorless genipin rich extracts, it is preferable to use a solvent or solvent combination with low solubility.

Methods for solid-liquid separation include regular filtration and centrifugation as well as press filtration and membrane cartridge filtering. You can also use a high-speed centrifuge to separate the liquid from the liquid. Or, you can settle and siphon off the liquid layer.

“Acids used to adjust pH can be any organic and inorganic acids that are suitable for the intended use.”

“Concentration is possible using any method that is known to the art. For example, it can be done by evaporating using a rotary vacuum, flash evaporator or an osmosis filter device with a suitable membrane.

“Properties and Uses of Genipin Rich Extract”

“Genipin rich extract is an off-white crystal or powder. If the purity is low, some batches might have a slight yellowish or greenish tint. Depending on the extraction method, the genipin content may reach as high as 97% (w/w). When HPLC analysis was performed, no geniposide or geniposidic acids, nor any other iridoid substances were detected in the genipin rich extract. The genipin rich extract’s remaining composition consists mainly of moisture, fat, and small amounts of acids or nitrogen-containing compounds. The balance is made up of carbohydrates as shown in the table below.

“Specification of Genipin Rich Materials”

“Genipin 30-97%nFatty acids 1.0%nFatt 5.0%nProtein1.0%nOrganic acids 0.5%”

“HPLC can be used for determining genipin content or performing other iridoid analyses.”

The powder’s genipin content is stable when kept at room temperature. After three months, the genipin level was less than 5%. Mixing genipin-rich extracts with compounds with a primary amino group will cause genipin to quickly react and create colorants and/or copolymers.

Extract with high genipin content dissolves easily in alcohol, alcohol-water combinations, and hot water. It is not solubilized in cold water.

“Colorant Production”

“The present invention also provides a method for manufacturing a blue colourant by using the genipin rich extract reaction and mixing water and amino acids. To speed up the reaction speed, heating can be used. The molar ratios between genipin rich extract and amino acids range from 1:0.5 to 1:10. Depending on the amino acid, there are a variety of blue shades: deep blue, violet, bright, greenish-blue and bright-blue. Blue colorant is made from genipin rich extract. It is heat- and acid-stable.

Similar blue colorants can also be created by combining genipin rich extract with other extracts and fruit and vegetable juices. These materials include dairy products and eggs, which contain amino acid, polypeptides and proteins. You can also make the blue color by combining the genipin rich extract with collagen, gelatin and chitosan. You can further concentrate the colorant or deposit it on clay or another carrier and use it in food, cosmetic (toothpaste and makeup), and textile (clothes).

“The present invention provides a method for manufacturing a red colourant using the genipin rich extract. Hydrolyzing the genipin-rich extraction removes a methyl group. This converts the genipin into genipinic acids. These react with additional organic acid and under anaerobic conditions to create red pigment. To accelerate the formation of red pigment, heating can be used. You can further purify the red solution on an ion exchange columns and concentrate it on a Rotary Vacuum Evaporator. Genipa is a heat-stable and stable pigment that is also stable at high pH.

Hydrolyzed genipin rich extract can be adjusted in pH with acids, preferably organic acids such as formic acid or lactic acid. Hydrolyzed solutions can be adjusted to pH between 3.5 and 5.0.

“The present invention also provides a method for making green colorant using the genipin rich extract. To create green color, genipin-rich extract can react to certain amino acids such as threonine and cysteine. It can also react with primary amino acids and combine with carotenoids and annatto pigments to produce green color. Genipa green, which can produce a heat-resistant green shade, is extremely useful in the food industry due to heat instability of the natural green pigment chlorophyll.

Similar green colorants can also be created by combining the genipin rich extract with other extracts, fruits and vegetable juice, dairy products, and egg products which are rich in amino acid, such as tryptophan, threonine and cysteine. To create green color, the genipin rich extract can be combined with collagen, gelatin and chitosan. It can also be mixed with annatto, carotenoids and turmeric pigments. You can further concentrate the colorant or deposit it on clay or another carrier and use it in food, cosmetic (toothpaste and makeup), and textile (clothes).

The present invention also provides a method to create other colorants such as purple, yellow, orange and brown by using the genipin rich extract. Mixing genipin rich extract with beet juice, carmine, and anthcyanin colorsants, and then combining them with amine-containing compounds can create purples and reds. You can create yellows and oranges by reacting genipin rich extract with pentoses such as xylose or ribose. When genipin reactions with primary amine groups are initiated, magnesium and calcium or metals having multi-valences can be involved.

“Cross-Linking Agent”

The present invention allows for new materials that contain approximately 97% genipin. Genipin-rich extracts can react with any compound containing a primary amino group, such as collagen and chitosan and glucosamine. This creates new texture materials that are used in the food, cosmetic, biomaterial and polymer industries.

The present invention also contains a cross-linking agent made from Genipa Americana, a natural plant. This agent can be used to replace synthesized chemicals such as succinaldehyde and glutaraldehyde. The toxicity of Genipin-rich extracts used as cross-linking agents is much lower than that of commonly used synthetic crosslinking reagents.

“Genipin rich extract can be used as a natural cross-linking agents for encapsulation production in both the food and pharmaceutical industries. Encapsulated materials may contain nutritional ingredients such as vitamin A, omega-3 oil, and conjugated linolenic oils, as well medicines. To make an encapsulation film, micro-membrane, or shell, you can use gelatin, collagen and whey proteins as well as casein, chitosan and other animal proteins. These products are biocompatible and have excellent thermal and mechanical stability.

“The following examples serve to illustrate the disclosure further, but they should not be considered as limiting.”

“Example 1”

“A genipin rich extract was created based on this process:

“Example 2”

“A genipin rich extract was created based on the following:

“Example 3”

“TABLE 1nStability genipin rich extractnStorage time (wks), Genipin, %w/wn0 8.3.9n4 86.0n6 853.3n12 84.7”

“The genipin material was stable throughout the testing period.”

“Example 4”

“Parameters Value\nHunter L-value 27.86\nHunter a-value 10.21\nHunter b-value 2.26\nWavelength (max, nm) 550.09\nAbsorption (max) 0.67314”

“Example 5”

“Parameters Value\nHunter L-value 27.42\nHunter a-value 9.46\nHunter b-value 2.32\nWavelength (max, nm) 549.97\nAbsorption (max) 0.94423”

“Example 6”

“Parameters Value\nHunter L-value 24.73\nHunter a-value 0.29\nHunter b-value 0.85\nWavelength (max, nm) 542.83\nAbsorption (max) 0.0170\nWavelength (2nd peak, nm) 595.06\nAbsorption (2nd peak) 0.88795”

“Example 7”

“Parameters L-Throenine L-Isoleucine L-Histidine\nDilution (g/ml) 0.50/100 0.30/100 0.10/100\nColor Green Green Blue\nHunter L-value 79.12 87.41 71.13\nHunter a-value ?5.91 ?3.42 ?7.82\nHunter b-value ?2.42 ?0.77 ?17.46\nWavelength (max, nm) 596.32 600.12 592.2\nAbsorption (max) 0.11914 0.06746 0.2537”

“Example 8”

“Parameters L.Alanine, XylosenColor orange-RednHunter L.value 25.12nHunter’s a-value 2.48nHunter’s b-value?0.22”

Summary for “Genipin-rich material” and its use

Today, synthetic chemicals such as colorants and cross-linking agents have a declining acceptance in the food cosmetics, animal feed, and textile industries. People prefer natural and organic ingredients in food, cosmetics, textile, biomaterial, and other products.

“Genipin can be described as a colorless compound. It is a member of the iridoid family. It is highly active chemically. It reacts instantly when mixed with compounds that have primary amine groups such as amino acids and collagen. The product can quickly turn blue, green or black if there is oxygen. Genipin, an iridoid ester, can be hydrolyzed into genipinic acids. This acid can also react with other compounds to produce red and brown colorants. Genipin colorants are stable to heat and pH. Genipin is a colorant that comes from plants. This makes it a great choice for baking and canning applications.

“Large amount of iridoids, such as geniposide, gardenoside, genipin-1-b-gentiobioside, geniposidic acid and genipin, can be found in Gardenia jasminoides Ellis fruit. Geniposide is an iridoid-related glycoside that makes up 7-8% of the fruit’s weight. However, only trace amounts are found in Gardenia fruits. The iridoids found in Gardenia fruits were traditionally extracted with methanol or alcohol, then separated on active carbon as yellow pigment, and then treated with enzymes with beta-glucosidic or proteolytic activity to transform glycoside iridoids into aglycone forms, genipinic or genipinic acids. “KR1020010096213A) – Genipinic or genipinic acids can then be combined with other compounds to make colorants.

“Genipin and other iridoid compounds, such as genipinic acid, genipin-gentiobioside, geniposide and geniposidic acid, are found also in the fruits and leaves of Genipa americana, also known as Genipap, or Huito, a tropical wild plant. Genipin can be found in mature fruits. Its quantity can range from 0 to 3.0% depending on the fruit’s ripeness. Genipin can be stored in the plant cell, but it will not become established there. Genipin reacts spontaneously with amino acids found in fruit pulp, and will change color in an environment that is either blue or black if the cell is damaged. Our previous patent application (US20090246343A1) described how to make coloring (blue-colored) fruit juice from Genipa Americana fruit pulp and juices of other fruits and vegetables. The natural acid-stable, blue juice has been widely used in the food and beverage industry. Lopes et al. (U.S. Pat. No. No. 7,927,637B2) used raw Genipa Americana fruit pulp unprocessed juice, mixed with glycine, or with glycine plus stearch, to create blue colorants. Patrice Andre (US20100196298A1) and a co-worker used coloring materials from the plant extract of Genipa Americana, Gardenia jasminoides or Rothmannia. These were bound to a solid substrate to create cosmetic compositions.

“Genipin can not only generate colorants but can also act as a cross-linking agent. Campbell et al. Campbell et al. discovered a biodegradable polymer that used genipin as a cross-linking agent (EP2093256A2). These plastics can be used in biological systems such as wound repair, implant, drug delivery and encapsulation, among other uses. Fujikawa et al. claimed (U.S. Pat. No. No. 4,983,524), the use of iridoid-aglycone (genipin) as a cross-linking agents to create immobilized enzyme beads for the food industry. R. Quijano and H. (US 20080195230A1) described the use of Genipin to fix whole, naturally occurring tissues in order to reduce immunogenicity and antigenicity, and to prevent the tissue from being enzymatically degraded when it is implanted into a host.

However, the process of producing pure genipin has been complicated in the past, with HPLC separation and a high cost. The art does not describe the method of making a stable extract from Genipa Americana. It is used as a cross-linking agent and natural colorant in food, drugs, nutritional supplements and personal care products.

The present disclosure reveals a method to produce stable, genipin rich extracts from Genipa Americana plants. This involves both aqueous and polar solvent extraction. The powder is a genipin rich extract with an off-white colour and a genipin content of about 97%.

“The present disclosure also provides applications of genipin rich extracts in natural colourant production and forming polmers for use in many areas such as food, drugs, nutritional supplement, cosmetics and animal feed. You can find examples of these uses in many patent documents, including U.S. Pat. No. No.

“All ratios and proportions are stated ‘by weight’ as they appear in this document. Except where otherwise stated. All patents, applications for patents and technical publications cited herein are also included by reference.”

The present disclosure reveals a method to produce stable genipin rich extracts from Genipa Americana plants. This involves both organic non-polar solvent and aqueous solvent extraction. The powder form of the genipin rich extract obtained is off-white and contains a genipin content of about 97%. Further, the present disclosure reveals the use of genipin rich extracts in the production natural heat-stable colorsants and as a cross-linking agent. This can be used in many areas such as food, drugs, nutritional supplements and personal care products.

“Starting Materials”

“Materials can be whole fruits, fruit pulp, juice, juice, juice concentrate, dried fruit powder, juice or fruit juice, water-insoluble parts of fruit, and Genipa americana leaves L.”

“Process for Genipin Rich Extraction”

“Next, the aqueous or concentrated genipin rich aqueous extraction may be further extracted using non-polar organic solvents. This involves suitable mixing (by shaking and agitation in a ratio of approximately 1:1). These non-polar organic solvents are polarity indexes between 0 and 5.0, with a water solubility of less than 30%. After the organic solvent phase has been separated from the aqueous phase, it can be siphoned or sucked using a high-speed centrifuge. Depending on the extraction efficiency, non-polar solvent extraction can be repeated 2 to 3 times. The genipin rich extracts can then be dried by evaporation. Organic solvents can be recycled and used for genipin extraction. The genipin-rich extract is the yellow-colored or off-white remaining solid. It contains a minimum of 70% w/w.

Geneipin-rich extracts can be either aqueous or from polar solvents. They are obtained from the raw materials described. The polar solvents are those that have water solubility of at least 100% and a polarity index greater then 5.0. These include water, acetic acids, methanol (ethanol, propanols, isopropanols, dimethyl sulfoxide), dimethyl formamide or water. While this list does not limit the solvents used, it is important to note that food safety is a consideration. Water, ethanol, iso-propanol and iso-propanol are preferred extracts for food use. Acetic, citric, and phosphate buffer solutions are preferred.

Geneipin-rich organic solvents can also be obtained from the aqueous and polar solvent extracts mentioned above. Non-polar organic solvents are those that have less than 30% water solubility and a greater polarity index of 0 to 5.0. These include ethyl and butyl alcohols, diethylethers, hexanes, 2-butanones, chloroforms, 1-butanol and methyl-t-butylethers, toluenes, carbon tetrachloride and trichloroethylene. While this list does not limit the solvents used, it is recommended that ethyl, butyl, and n?butanol be preferred due to their food safety.

Organic solvent extracts from the raw materials described may also be considered genepin-rich extracts. These organic solvents can be any with a polarity index lower than 6.0 or mixtures of them in different ratios. To obtain colorless genipin rich extracts, it is preferable to use a solvent or solvent combination with low solubility.

Methods for solid-liquid separation include regular filtration and centrifugation as well as press filtration and membrane cartridge filtering. You can also use a high-speed centrifuge to separate the liquid from the liquid. Or, you can settle and siphon off the liquid layer.

“Acids used to adjust pH can be any organic and inorganic acids that are suitable for the intended use.”

“Concentration is possible using any method that is known to the art. For example, it can be done by evaporating using a rotary vacuum, flash evaporator or an osmosis filter device with a suitable membrane.

“Properties and Uses of Genipin Rich Extract”

“Genipin rich extract is an off-white crystal or powder. If the purity is low, some batches might have a slight yellowish or greenish tint. Depending on the extraction method, the genipin content may reach as high as 97% (w/w). When HPLC analysis was performed, no geniposide or geniposidic acids, nor any other iridoid substances were detected in the genipin rich extract. The genipin rich extract’s remaining composition consists mainly of moisture, fat, and small amounts of acids or nitrogen-containing compounds. The balance is made up of carbohydrates as shown in the table below.

“Specification of Genipin Rich Materials”

“Genipin 30-97%nFatty acids 1.0%nFatt 5.0%nProtein1.0%nOrganic acids 0.5%”

“HPLC can be used for determining genipin content or performing other iridoid analyses.”

The powder’s genipin content is stable when kept at room temperature. After three months, the genipin level was less than 5%. Mixing genipin-rich extracts with compounds with a primary amino group will cause genipin to quickly react and create colorants and/or copolymers.

Extract with high genipin content dissolves easily in alcohol, alcohol-water combinations, and hot water. It is not solubilized in cold water.

“Colorant Production”

“The present invention also provides a method for manufacturing a blue colourant by using the genipin rich extract reaction and mixing water and amino acids. To speed up the reaction speed, heating can be used. The molar ratios between genipin rich extract and amino acids range from 1:0.5 to 1:10. Depending on the amino acid, there are a variety of blue shades: deep blue, violet, bright, greenish-blue and bright-blue. Blue colorant is made from genipin rich extract. It is heat- and acid-stable.

Similar blue colorants can also be created by combining genipin rich extract with other extracts and fruit and vegetable juices. These materials include dairy products and eggs, which contain amino acid, polypeptides and proteins. You can also make the blue color by combining the genipin rich extract with collagen, gelatin and chitosan. You can further concentrate the colorant or deposit it on clay or another carrier and use it in food, cosmetic (toothpaste and makeup), and textile (clothes).

“The present invention provides a method for manufacturing a red colourant using the genipin rich extract. Hydrolyzing the genipin-rich extraction removes a methyl group. This converts the genipin into genipinic acids. These react with additional organic acid and under anaerobic conditions to create red pigment. To accelerate the formation of red pigment, heating can be used. You can further purify the red solution on an ion exchange columns and concentrate it on a Rotary Vacuum Evaporator. Genipa is a heat-stable and stable pigment that is also stable at high pH.

Hydrolyzed genipin rich extract can be adjusted in pH with acids, preferably organic acids such as formic acid or lactic acid. Hydrolyzed solutions can be adjusted to pH between 3.5 and 5.0.

“The present invention also provides a method for making green colorant using the genipin rich extract. To create green color, genipin-rich extract can react to certain amino acids such as threonine and cysteine. It can also react with primary amino acids and combine with carotenoids and annatto pigments to produce green color. Genipa green, which can produce a heat-resistant green shade, is extremely useful in the food industry due to heat instability of the natural green pigment chlorophyll.

Similar green colorants can also be created by combining the genipin rich extract with other extracts, fruits and vegetable juice, dairy products, and egg products which are rich in amino acid, such as tryptophan, threonine and cysteine. To create green color, the genipin rich extract can be combined with collagen, gelatin and chitosan. It can also be mixed with annatto, carotenoids and turmeric pigments. You can further concentrate the colorant or deposit it on clay or another carrier and use it in food, cosmetic (toothpaste and makeup), and textile (clothes).

The present invention also provides a method to create other colorants such as purple, yellow, orange and brown by using the genipin rich extract. Mixing genipin rich extract with beet juice, carmine, and anthcyanin colorsants, and then combining them with amine-containing compounds can create purples and reds. You can create yellows and oranges by reacting genipin rich extract with pentoses such as xylose or ribose. When genipin reactions with primary amine groups are initiated, magnesium and calcium or metals having multi-valences can be involved.

“Cross-Linking Agent”

The present invention allows for new materials that contain approximately 97% genipin. Genipin-rich extracts can react with any compound containing a primary amino group, such as collagen and chitosan and glucosamine. This creates new texture materials that are used in the food, cosmetic, biomaterial and polymer industries.

The present invention also contains a cross-linking agent made from Genipa Americana, a natural plant. This agent can be used to replace synthesized chemicals such as succinaldehyde and glutaraldehyde. The toxicity of Genipin-rich extracts used as cross-linking agents is much lower than that of commonly used synthetic crosslinking reagents.

“Genipin rich extract can be used as a natural cross-linking agents for encapsulation production in both the food and pharmaceutical industries. Encapsulated materials may contain nutritional ingredients such as vitamin A, omega-3 oil, and conjugated linolenic oils, as well medicines. To make an encapsulation film, micro-membrane, or shell, you can use gelatin, collagen and whey proteins as well as casein, chitosan and other animal proteins. These products are biocompatible and have excellent thermal and mechanical stability.

“The following examples serve to illustrate the disclosure further, but they should not be considered as limiting.”

“Example 1”

“A genipin rich extract was created based on this process:

“Example 2”

“A genipin rich extract was created based on the following:

“Example 3”

“TABLE 1nStability genipin rich extractnStorage time (wks), Genipin, %w/wn0 8.3.9n4 86.0n6 853.3n12 84.7”

“The genipin material was stable throughout the testing period.”

“Example 4”

“Parameters Value\nHunter L-value 27.86\nHunter a-value 10.21\nHunter b-value 2.26\nWavelength (max, nm) 550.09\nAbsorption (max) 0.67314”

“Example 5”

“Parameters Value\nHunter L-value 27.42\nHunter a-value 9.46\nHunter b-value 2.32\nWavelength (max, nm) 549.97\nAbsorption (max) 0.94423”

“Example 6”

“Parameters Value\nHunter L-value 24.73\nHunter a-value 0.29\nHunter b-value 0.85\nWavelength (max, nm) 542.83\nAbsorption (max) 0.0170\nWavelength (2nd peak, nm) 595.06\nAbsorption (2nd peak) 0.88795”

“Example 7”

“Parameters L-Throenine L-Isoleucine L-Histidine\nDilution (g/ml) 0.50/100 0.30/100 0.10/100\nColor Green Green Blue\nHunter L-value 79.12 87.41 71.13\nHunter a-value ?5.91 ?3.42 ?7.82\nHunter b-value ?2.42 ?0.77 ?17.46\nWavelength (max, nm) 596.32 600.12 592.2\nAbsorption (max) 0.11914 0.06746 0.2537”

“Example 8”

“Parameters L.Alanine, XylosenColor orange-RednHunter L.value 25.12nHunter’s a-value 2.48nHunter’s b-value?0.22”

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