geniposide
genipin 1-glucoside
Identification
| Name | geniposide |
| IUPAC | methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate |
| CAS Number | 24512-63-8 |
| FDA UNII | 145295QLXY |
| Molecular Formula | C17 H24 O10 |
| Molecular Weight | 388.37028000 |
| MDL Number | MFCD16036219 |
| Nikkaji Number | J16.693F |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 641.40 °C. @ 760.00 mm Hg (est) |
| Flash Point | 449.00 °F. TCC ( 231.50 °C. ) (est) |
| logP (o/w) | -1.920 (est) |
| Soluble in | water, 3.724e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for geniposide usage levels up to | not for fragrance use. |
| Recommendation for geniposide flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)-
cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S-(1alpha,4aalpha,7aalpha))-
genipin 1-glucoside
jasminoidin
methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
PubMed:
Influence of the Stage of Ripeness on the Composition of Iridoids and Phenolic Compounds in Genipap (Genipa americana L.).
PubMed:
Effects of intestinal microbiota on the bioavailability of geniposide in rats.
PubMed:
Genipin inhibits IL-1β-induced CCL20 and IL-6 production from human periodontal ligament cells.
PubMed:
Preparative separation of crocins and geniposide simultaneously from gardenia fruits using macroporous resin and reversed-phase chromatography.
PubMed:
Variations in target gene expression and pathway profiles in the mouse hippocampus following treatment with different effective compounds for ischemia-reperfusion injury.
PubMed:
Enrichment and purification of gardenia yellow from Gardenia jasminoides var. radicans Makino by column chromatography technique.
PubMed:
Monoamine Oxidase and Dopamine β-Hydroxylase Inhibitors from the Fruits of Gardenia jasminoides.
PubMed:
Eucommia ulmoides bark protects against renal injury in cadmium-challenged rats.
PubMed:
Elucidation of anti-inflammatory potencies of Eucommia ulmoides bark and Plantago asiatica seeds.
PubMed:
Biotransformation of ginsenoside Rb1, crocin, amygdalin, geniposide, puerarin, ginsenoside Re, hesperidin, poncirin, glycyrrhizin, and baicalin by human fecal microflora and its relation to cytotoxicity against tumor cells.
PubMed:
Metabolism and pharmacokinetics of genipin and geniposide in rats.
PubMed:
Simultaneous determination of geniposide and its metabolites genipin and genipinine in culture of Aspergillus niger by HPLC.
PubMed:
A 13-week oral dose subchronic toxicity study of gardenia yellow containing geniposide in rats.
PubMed:
[Research and development of Fructus Gardeniae].
PubMed:
Crocetin esters, picrocrocin and its related compounds present in Crocus sativus stigmas and Gardenia jasminoides fruits. Tentative identification of seven new compounds by LC-ESI-MS.
PubMed:
Isolation and characterization of water-soluble intermediates of blue pigments transformed from geniposide of Gardenia jasminoides.
PubMed:
Genotoxicity of gardenia yellow and its components.
PubMed:
Physical stability of the blue pigments formed from geniposide of gardenia fruits: effects of pH, temperature, and light.
PubMed:
Modulation of cytochrome P-450-dependent monooxygenases, glutathione and glutathione S-transferase in rat liver by geniposide from Gardenia jasminoides.
PubMed:
Hepatotoxicity of geniposide in rats.