6902-77-8

Basic information

• Product Name: 1,4a,5,7a-Tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester
• Synonyms: Methyl (1R,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate;cyclopenta(c)pyran-4-carboxylicacid,1,4a-alpha,5,7a-alpha-tetrahydro-1-hydrox;GENIPIN;1,4a,5,7a-tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester;Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate;(1R)-1,4aα,5,7aα-Tetrahydro-1-hydroxy-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid methyl ester;(1R)-1,4aα,5,7aα-Tetrahydro-1α-hydroxy-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid methyl ester;Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-
• CAS NO: 6902-77-8
• Molecular Formula: C₁₁H₁₄O₅
• Molecular Weight: 226.23
• EINECS: 300-006-4
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 6902-77-8.mol

Chemical Properties

• Melting Point: 118.0 to 123.0 °C
• Boiling Point: 287.83°C (rough estimate)
• Flash Point: 164.9 °C
• Appearance: /
• Density: 1.1230 (rough estimate)
• Vapor Pressure: 1.17E-08mmHg at 25°C
• Refractive Index: 1.4720 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO: ≥25mg/mL
• PKA: 12.06±0.60(Predicted)
• CAS DataBase Reference: 1,4a,5,7a-Tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4a,5,7a-Tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester(6902-77-8)
• EPA Substance Registry System: 1,4a,5,7a-Tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester(6902-77-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 3/14-36/37/39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: GY5828000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 6902-77-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 6902-77-8 differently. You can refer to the following data:
1. Genipin is an active aglycone derived from an iridoid glycoside called geniposide, which is found in the fruit of Gardenia jasminoides Ellis. Genipin is a hydrolytic product of geniposide. Genipin has been used in traditional Chinese medicine. Genipin is
2. Genipin is an inhibitor of uncoupling protein 2 (UCP2).
3. Genipin has been used:in chemosensitivity assayin the preparation of recombinant human (rh)-odontogenic ameloblast-associated protein (ODAM) -impregnated collagen gel and in vitro mineralization assayin genipin gel preparation

General Description

Genipin is a natural cross linking agent, which is extracted from gardenia fruit. It prevents lipid peroxidation and production of nitric oxide. Genipin protects the hippocampal neurons from the toxicity of Alzheimer′s amyloid β protein. It has anti-inflammatory and anti-angiogenesis effects. Genipin is involved in drug delivery system.

Biochem/physiol Actions

Genipin stimulates insulin secretion in UCP2-dependent manner (Uncoupling protein 2). Genipin is a protein, collagen, gelatin, and chitosan cross-linker.

InChI:InChI=1/C11H14O5/c1-15-10(13)8-5-16-11(14)9-6(4-12)2-3-7(8)9/h2,5,7,9,11-12,14H,3-4H2,1H3/t7-,9-,11-/m1/s1

Upstream product

• 24512-63-8 geniposide 
• 67-48-1 choline chloride 
• 1174680-01-3 genipin 1-O-β-D-isomaltoside 
• 24512-63-8 geniposide 

Downstream Products

• 116306-66-2 (1S,4aS,7aS)-1-(tert-Butyl-dimethyl-silanyloxy)-7-phenylsulfanylmethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 
• 116287-89-9 (1S,4aS,7aS)-7-Benzenesulfinylmethyl-1-(tert-butyl-dimethyl-silanyloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 
• 69977-52-2 1-methoxygenipin 
• 1246811-62-0 C₁₈H₂₀O₅S 
• 1246811-53-9 C₁₈H₂₀O₄S 

Relevant articles and documents

Physical stability of the blue pigments formed from geniposide of gardenia fruits: Effects of ph, temperature, and light

Fruits of Gardenia jasminoides contain geniposide which can be transformed to blue pigments by a simple modification. Colorless geniposide obtained from gardenia, fruits by charcoal and silica gel column chromatographies was hydrolyzed with β-glucosidase to yield genipin. The resulting genipin was transformed to blue pigments by reaction with amino acids (glycine, lysine, or phenylalanine). The stability of the blue pigments against heat, light, and pH was studied to examine the blue dye for possible use as' a value-added food colorant. Thermal degradation reactions at temperatures of 60-90 °C were carried out at different pH levels within the range 5.0-9.0 (pH 5.0, acetate buffer; pH 7.0, phosphate buffer; and pH 9.0, CHES buffer). The blue pigments remained Stable after 10 h at temperatures of 60-90 °c, and in some cases, more new pigments formed. The pigments were more stable at alkaline pH than neutral and acidic pH. Similarly, the pigments were stable under light irradiance of 5000-20 000 lux. In this case, pH effect was not significant.

Iridoid glycosides from Gardeniae Fructus for treatment of ankle sprain

The iridoid glycosides, genipin 1-O-β-d-isomaltoside (1) and genipin 1,10-di-O-β-d-glucopyranoside (2), together with six known iridoid glycosides, genipin 1-O-β-d-gentiobioside (3), geniposide (4), scandoside methyl ester (5), deacetylasperulosidic acid

IRIDOIDS OF GARRYA ELLIPTICA AS PLANT GROWTH INHIBITORS

Extracts from catkins of Garrya elliptica inhibit the growth of wheat embryos.The components responsible for this activity have been identified as the iridoids geniposide and geniposidic acid together with their aglucones.Key Word Index - Garrya elliptica; Garryaceae; iridoids; aglucones; genipin; geniposide; geniposide acid; plant growth inhibitors.

Two new iridoid glycosides from Gardeniae Fructus

Two new iridoid glycosides, genipin 1,10-di-O-α-L-rhamnoside (1) and genipin 1,10-di-O-β-D-xylopyranoside (2), along with thirteen known compounds (3–15) were isolated from Gardeniae Fructus. Their structures were elucidated by physical data analyses such as NMR, UV, IR, HR-ESI-MS, as well as chemical hydrolysis. All compounds were tested for their tyrosinase inhibitory and antioxidant activities. At a concentration of 25 μM, compound 13 showed obvious mushroom tyrosinase inhibition activity with % inhibition value of 36.52 ± 1.98%, with kojic acid used as the positive control (46.09 ± 1.29%). At a concentration of 1 mM, compounds 8 and 9 exhibited considerable DPPH radical scavenging activities, with radical scavenging rates of 48.54 ± 0.47%, 58.59 ± 0.39%, respectively, with L-ascorbic acid used as the positive control (59.02 ± 0.77%).

A PROCESS FOR PRODUCING GARDENIA BLUE PIGMENT FORM GENIPOSIDE

A process for producing the gardenia blue pigment comprising treating geniposide with a glycosidase to obtain a hydrolysate, extracting the hydrolysate with a solvent and removing the solvent after the extraction to obtain a product comprising genipin, reacting the product comprising genipin with an amino acid and/or a salt thereof under an atmosphere of inert gas, and introducing oxygen after genipin is consumed to produce the gardenia blue pigment. The process is easy-to-workup and suitable for industry and the obtained gardenia blue pigment is bright and suitable for industrial application.

An acid-stable β-glucosidase from Aspergillus aculeatus: Gene expression, biochemical characterization and molecular dynamics simulation

β-Glucosidases hydrolyze terminal, non-reducing β-D-glucosyl residues and thereby release β-D-glucose. They have applications in the production of biofuels, beverages and pharmaceuticals. In this study, a β-glucosidase derived from Aspergillus aculeatus (BGLA) was expressed, characterized, and the molecular mechanism of its acid denaturation was comprehensively probed. BGLA exhibited maximal activity at pH 5.0–6.0. Its optimal temperature was 70 °C. Its enzyme activity was enhanced by Mg2+, Ca2+ and Ba2+, while Cu2+, Mn2+, Zn2+, Fe2+ and Fe3+ had a negative effect. BGLA showed activity on a broad range of substrates including salicin, cellobiose, arbutin, geniposide and polydatin. Finally, the acid-denaturation mechanism of BGLA was probed using molecular dynamics (MD) simulations. The results of simulation at pH 2.0 imply that the contact number, solvent accessible surface area and number of hydrogen bonds in BGLA decreased greatly. Moreover, the distance between the residues Asp280 and Glu509 that are part of the active site increased, which eventually destroyed the enzyme's catalytic activity. These MD results explain the molecular mechanism of acid denaturation of BGLA, which will greatly benefit the rational design of more acid-stable β-glucosidase variants in the future.

BICYCLIC COMPOUND AND PHARMACEUTICAL COMPOSITION THEREOF FOR TREATING STROKE AND USE THEREOF

The present disclosure relates to a bicyclic compound, a pharmaceutical composition thereof, and its novel use. More particularly, the present disclosure relates to the bicyclic compound according to Formula I or Formula II, the pharmaceutical composition for treating a stroke, and the use of the bicyclic compound treating the stroke.

Enhancement of active compound, genipin, from Gardeniae Fructus using immobilized glycosyl hydrolase family 3 β-glucosidase from Lactobacillus antri

Geniposide is an iridoid glycoside, which is abundant in Gardeniae Fructus. Despite the various pharmaceutical effects of geniposide on a human body, its hydrolysis into a smaller molecule, genipin, by β-glucosidase produced by bacteria in the intestines is particularly important to improve geniposide uptake into the body. Since geniposide is much more abundant in Gardeniae Fructus than its aglycone genipin, we herein transformed geniposide into genipin using purified recombinant β-glucosidase from Lactobacillus antri (rBGLa), which was expressed in Escherichia coli to enhance the genipin content. Purified rBGLa was characterized using p-nitrophenyl β-d-glucopyranoside, and the optimal temperature and pH for its β-glucosidase activity were found to be 45?°C and 6.0. When the enzyme was immobilized, rBGLa was active at higher temperatures than the free enzyme, and we confirmed that its stability upon changes in pH and temperature was highly improved. Using 0.5?μg/mL free rBGLa, single compound of 0.4?mM geniposide was efficiently converted into genipin within 2?h, and the immobilized rBGLa also successfully transformed geniposide in a hot-water extract of Gardeniae Fructus into the aglycone, which makes it applicable to the food and pharmaceutical industries.

A NEW PROCESS FOR PRODUCING GARDENIA BLUE PIGMENT

A process for producing the gardenia blue pigment is provided. The process is easy to operate and suitable for industry and the obtained gardenia blue pigment is bright and suitable for industrial application.

NEW GARDENIA BLUE PIGMENT, PREPARATION AND USE THEREOF

A gardenia blue pigment is derived from a reaction of genipin with an amino acid. It is brighter than commercial gardenia blue pigment and suitable for industrial application. A process for producing the gardenia blue pigment and the use thereof in food and beverage industries are also provided.