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Cas Database

6902-77-8

6902-77-8

Identification

Synonyms:Cyclopenta[c]pyran-4-carboxylicacid, 1,4a,5,7a-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl ester, [1R-(1a,4aa,7aa)]-;Cyclopenta[c]pyran-4-carboxylic acid, 1,4aa,5,7aa-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl ester (8CI);Genipin(6CI);(+)-Genipin;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowed

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:Usbiological
  • Product Description:Genipin
  • Packaging:20mg
  • Price:$ 280
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:Genipin
  • Packaging:50mg
  • Price:$ 100
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Genipin >97.0%(GC)
  • Packaging:25mg
  • Price:$ 61
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Genipin >97.0%(GC)
  • Packaging:100mg
  • Price:$ 174
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Methyl(1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate 96%
  • Packaging:5 g
  • Price:$ 594
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Methyl(1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate 96%
  • Packaging:1 g
  • Price:$ 207
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Genipin ≥98% (HPLC), powder
  • Packaging:25mg
  • Price:$ 113
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Genipin ≥98% (HPLC), powder
  • Packaging:125mg
  • Price:$ 445
  • Delivery:In stock
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:Genipin 98%
  • Packaging:20 mg
  • Price:$ 425
  • Delivery:In stock
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Genipin >99%
  • Packaging:250 mg
  • Price:$ 500
  • Delivery:In stock
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Relevant articles and documentsAll total 15 Articles be found

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

Paik, Young-Sook,Lee, Chang-Min,Cho, Man-Ho,Hahn, Tae-Ryong

, p. 430 - 432 (2001)

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.

IRIDOIDS OF GARRYA ELLIPTICA AS PLANT GROWTH INHIBITORS

Cameron, Donald W.,Feutrill, Geoffrey I.,Perlmutter, Patrick,Sasse, Jenneth M.

, p. 533 - 536 (1984)

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

Shu, Penghua,Yu, Mengzhu,Zhu, Huiqing,Luo, Yuehui,Li, Yamin,Li, Nianci,Zhang, Hui,Zhang, Jialong,Liu, Guangwei,Wei, Xialan,Yi, Wenhan

, (2021/02/26)

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

-

Page/Page column 6, (2018/03/06)

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.

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

Kim, Young Soo,Lee, Chung-Jo,Ma, Jin Yeul

, (2017/03/24)

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.

Process route upstream and downstream products

Process route

choline chloride
67-48-1

choline chloride

1,2-dipalmotoyl-3-sn-phosphatidylgenipin

1,2-dipalmotoyl-3-sn-phosphatidylgenipin

1,2-dipalmitoyl-rac-glycero-3-phosphatidylcholine
2644-64-6,2797-68-4

1,2-dipalmitoyl-rac-glycero-3-phosphatidylcholine

Conditions
Conditions Yield
With calcium chloride; In ethyl acetate; Ambient temperature; phospholipase D from Streptomyces sp., acetate buffer, pH 5.6; phospholipase-D-catalysed transphosphatidylation reactions;
Conditions
Conditions Yield
With β-glucosidase from Aspergillus aculeatus; water; In aq. phosphate buffer; at 70 ℃; for 0.333333h; pH=5; Enzymatic reaction;
genipin 1,10-di-O-α-L-rhamnoside

genipin 1,10-di-O-α-L-rhamnoside

D-xylose
58-86-6

D-xylose

Conditions
Conditions Yield
With hydrogenchloride; In methanol; for 2h; Reflux;
genipin 1,10-di-O-β-D-xylopyranoside

genipin 1,10-di-O-β-D-xylopyranoside

D-xylose
58-86-6

D-xylose

Conditions
Conditions Yield
With hydrogenchloride; In methanol; for 2h; Reflux;
Conditions
Conditions Yield
With water; In dichloromethane; at 37 ℃; for 24h; Enzymatic reaction;
84%
With immobilized β-glucosidase; In ethyl acetate; at 55 ℃; pH=4.5; aq. acetate buffer;
63.08%
With acetate buffer; β-glucosidase; at 37 ℃; for 5h; pH=5.0;
0.5 g
Multi-step reaction with 2 steps
1: 1.) aq. NaIO4, 2.) NaBH4 / 1.) RT, 2 h, 2.) RT, 2 h
2: 6 N aq. HCl / diethyl ether / 4 h / Ambient temperature
With hydrogenchloride; sodium tetrahydroborate; sodium periodate; In diethyl ether;
With β-glucosidase; Enzymatic reaction;
With recombinant β-glucosidase from Lactobacillus antri DSM 16041; water; In aq. phosphate buffer; at 45 ℃; for 2h; pH=6; Reagent/catalyst; Enzymatic reaction;
With cellobiase; In aq. phosphate buffer; at 50 ℃; for 19h; pH=4.0; Reagent/catalyst; pH-value; Enzymatic reaction;
With disodium hydrogenphosphate; citric acid; In water; at 50 ℃; for 19h; pH=4; Concentration; Enzymatic reaction;
With cellobiase; In aq. phosphate buffer; at 50 ℃; for 10h; pH=4; Enzymatic reaction;
Conditions
Conditions Yield
With β-glucosidase; In water; at 23 ℃; for 9h;
10.5 mg
genipin 1,10-di-O-β-D-glucopyranoside

genipin 1,10-di-O-β-D-glucopyranoside

Conditions
Conditions Yield
With naringinase; at 37 ℃; for 3h; pH=5.5; aq. acetate buffer; Enzymatic reaction;
genipin 1-O-β-D-isomaltoside
1174680-01-3

genipin 1-O-β-D-isomaltoside

Conditions
Conditions Yield
With naringinase; at 37 ℃; for 3h; pH=5.5; aq. acetate buffer; Enzymatic reaction;
(1S,4aS,7aS)-1-[(S)-2-Hydroxy-1-(2-hydroxy-1-hydroxymethyl-ethoxy)-ethoxy]-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

(1S,4aS,7aS)-1-[(S)-2-Hydroxy-1-(2-hydroxy-1-hydroxymethyl-ethoxy)-ethoxy]-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions
Conditions Yield
With hydrogenchloride; In diethyl ether; for 4h; Yield given; Ambient temperature;
Conditions
Conditions Yield
With β-glucosidase; In water; at 37 ℃; for 2h;

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  • Simagchem Corporation
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  • Shaanxi BLOOM TECH Co.,Ltd
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