27745-20-6

Basic information

• Product Name: Geniposide
• Synonyms: Cyclopenta[c]pyran-4-carboxylicacid, 1-(b-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-,methyl ester, [1S-(1a,4aa,7aa)]-; Geniposide (8CI)
• CAS NO: 27745-20-6
• Molecular Formula: C17H24O10
• Molecular Weight: 388.36646
• EINECS: 300-006-5
• Mol File: 27745-20-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 641.4°Cat760mmHg
• Flash Point: 231.5°C
• Appearance: /
• Density: 1.54g/cm³
• CAS DataBase Reference: Geniposide(CAS DataBase Reference)
• NIST Chemistry Reference: Geniposide(27745-20-6)
• EPA Substance Registry System: Geniposide(27745-20-6)

Safety Data

• Hazardous Substances Data: 27745-20-6(Hazardous Substances Data)

Usage

Description

Geniposide is a natural compound found in a variety of plants, including gardenia fruit and blackberry lily, with potential pharmacological and therapeutic properties. It is primarily known for its anti-inflammatory, antioxidant, and neuroprotective effects.
Used in Pharmaceutical Industry:
Geniposide is used as a therapeutic agent for its anti-inflammatory, antioxidant, and neuroprotective properties, which can protect against damage to liver and kidney cells, reduce inflammation in the body, and potentially improve cognitive function.
Used in Treatment of Diabetes:
Geniposide is used as a treatment for diabetes due to its potential to improve glucose metabolism and insulin sensitivity.
Used in Cardiovascular Disease Treatment:
Geniposide is used as a treatment for cardiovascular disease due to its potential to improve blood flow and reduce oxidative stress.
Used in Neurodegenerative Disorders Treatment:
Geniposide is used as a treatment for neurodegenerative disorders due to its potential to protect neurons and reduce inflammation in the brain.

Upstream product

• 70094-79-0 genipin 
• 1141938-70-6 7-(2,2-dimethyl-propionyloxymethyl)-1-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 
• 27741-01-1 geniposidic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 186581-53-3 diazomethane 

Downstream Products

• 49776-64-9 geniposide penta-acetate 
• 78924-52-4 4',6'-O-benzylidene-geniposide 
• 27741-01-1 geniposidic acid 
• 42830-26-2 6,7-dihydroapodantheroside 
• 256221-90-6 (S)-1-((1S,2R,3S)-2,3-Bis-hydroxymethyl-cyclopentyl)-ethane-1,2-diol 
• 78924-53-5 4',6'-O-benzylidene-2',3',10-tri-O-benzyl-geniposide 
• 78924-57-9 (2aR,3R,4aS,7aS,7bS)-3-Hydroxy-2a,3,4,4a,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]indene-5-carboxylic acid methyl ester 
• 78924-57-9 (2aR,3S,4aS,7aS,7bS)-3-Hydroxy-2a,3,4,4a,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]indene-5-carboxylic acid methyl ester 
• 42830-27-3 (1S,4aS,7R,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 
• 69977-52-2 1-methoxygenipin 
• 492-61-5 β-D-glucose 
• 70094-79-0 genipin 
• 26660-57-1 deoxyloganin 
• 27741-01-1 geniposidic acid 

Relevant articles and documents

Discovery of Glycosylated Genipin Derivatives as Novel Antiviral, Insecticidal, and Fungicidal Agents

A series of novel genipin glycoside derivatives incorporating 11 glycosidic moieties at either the 1 or 10 position of genipin were designed and synthesized. These compounds exhibited moderate to excellent inhibitory activities against tobacco mosaic virus. Especially, the in vitro and in vivo activities of compounds 6e, 7c, 7d, 7f, 7h, and 7i were comparable to that of ribavirin. In particular, compound 7c, the mannosyl derivative of genipin at the 10 position, showed the best activity. The series of genipin glycosyl derivatives also displayed fungicidal activities against 14 kinds of phytopathogenic fungi, especially for Rhizoctonia cerealis and Sclerotinia sclerotiorum. Moreover, compound 6h exhibited good insecticidal activity against diamondback moth; compounds 7b, 7c, and 7g exhibited moderate insecticidal activity against three kinds of Lepidoptera pests (oriental armyworm, cotton bollworm, and corn borer); and compound 7e showed excellent larvacidal activities against mosquito.

Hair dyeing by iridoid glycosides and aglycons thereof

A method of dyeing hair which comprises contacting hair with an iridoid glycoside or an aglycon thereof.

IRIDOID GLUCOSIDES IN AVICENNIA MARINA

Key Word Index - Avicennia marina; Verbenaceae; iridoids; geniposidic acid; mussaenosidic acid; 2'-cinnamoylmussaenosidic acid; 10-O-(5-phenyl-2,4-pentadienoyl)-geniposidic acid; 7-O-(5-phenyl-2,4-pentadienoyl)-8-epiloganic acid. - 2'-Cinnamoyl-mussaenoside , 10-O-(5-phenyl-2,4-pentadienoyl)-geniposide, 7-O-(5-phenyl-2,4-pentadienoyl)-8-epiloganin, and the known iridoids geniposide and mussaenoside have been isolated from a methylated extract of the leaves of Avicennia marina.Evidence is presented that the iridoids occur as the free acids in the plant.The taxonomic significance of these findings is discussed.