andrographolide
(3E,4S)-4-hydroxy-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl]ethylidene}dihydrofuran-2(3H)-one
Identification
| Name | andrographolide |
| IUPAC | (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one |
| CAS Number | 5508-58-7 |
| EINECS | 226-852-5 |
| FDA UNII | 410105JHGR |
| Molecular Formula | C20 H30 O5 |
| Molecular Weight | 350.45510000 |
| MDL Number | MFCD07778082 |
| Nikkaji Number | J3.154.642G |
| Beilstein | 0042762 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 225.00 to 226.00 °C. @ 760.00 mm Hg |
| Boiling Point | 557.32 °C. @ 760.00 mm Hg (est) |
| Flash Point | 384.00 °F. TCC ( 195.50 °C. ) (est) |
| logP (o/w) | 0.424 (est) |
| Soluble in | water, 146.9 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | skin conditioning |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 11460 mg/kg |
| 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 | cosmetic ingredient for skin conditioning |
| Recommendation for andrographolide usage levels up to | not for fragrance use. |
| Recommendation for andrographolide flavor usage levels up to | not for flavor use. |
BOC Sciences
Best of Chemicals Supplier
Quality supplier of research chemicals and biochemicals including inhibitors, building blocks, GMP Products, impurities and metabolites, APIs for Veterinary, Natural Compounds, ADCs, Stem Cell Molecul...
Potential Uses
Natural Occurrence
Synonyms
(S,E)-4-
hydroxy-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-decahydronaphthalen-1-yl)ethylidene)-dihydrofuran-2(3H)-one
(S)-4-
hydroxy-3-[2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-hydroxymethyl-5,8a-dimethyl-2-methylene-decahydro-naphthalen-1-yl)-eth-(E)-ylidene]-dihydro-furan-2-one
(3E,4S)-4-
hydroxy-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl]ethylidene}dihydrofuran-2(3H)-one
(3E,4S)-4-
hydroxy-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl]ethylidene}dihydrofuran-2(3H)-one
(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6
hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
PubMed:
Positive therapy of andrographolide in vocal fold leukoplakia.
PubMed:
Andrographolide induces autophagic cell death in human liver cancer cells through cyclophilin D-mediated mitochondrial permeability transition pore.
PubMed:
Simultaneous determination of 9-dehydro-17-hydro-andrographolide and sodium 9-dehydro-17-hydro-andrographolide-19-yl sulfate in rat plasma by UHPLC-ESI-MS/MS after administration of xiyanping injection: application to a pharmacokinetic study.
PubMed:
Evaluation of the effect of andrographolide on atherosclerotic rabbits induced by Porphyromonas gingivalis.
PubMed:
Potential anti-angiogenic sulfates of andrographolide.
PubMed:
The genotoxicity and cytotoxicity assessments of andrographolide in vitro.
PubMed:
Andrographolide-induced pi class of glutathione S-transferase gene expression via PI3K/Akt pathway in rat primary hepatocytes.
PubMed:
Enhancing bioavailability and hepatoprotective activity of andrographolide from Andrographis paniculata, a well-known medicinal food, through its herbosome.
PubMed:
Cytochrome P450 induction properties of food and herbal-derived compounds using a novel multiplex RT-qPCR in vitro assay, a drug-food interaction prediction tool.
PubMed:
Effects of andrographolide on sexual functions, vascular reactivity and serum testosterone level in rodents.
PubMed:
Induction of heme oxygenase 1 and inhibition of tumor necrosis factor alpha-induced intercellular adhesion molecule expression by andrographolide in EA.hy926 cells.
PubMed:
Quantification of andrographolide sodium bisulphite in urine after intravenous injection to rats by LC-MS/MS.
PubMed:
Andrographolide inhibits ICAM-1 expression and NF-κB activation in TNF-α-treated EA.hy926 cells.
PubMed:
Andrographolide and 14-deoxy-11,12-didehydroandrographolide from Andrographis paniculata attenuate high glucose-induced fibrosis and apoptosis in murine renal mesangeal cell lines.
PubMed:
Activation of the cAMP/CREB/inducible cAMP early repressor pathway suppresses andrographolide-induced gene expression of the pi class of glutathione S-transferase in rat primary hepatocytes.
PubMed:
The human bitter taste receptor hTAS2R50 is activated by the two natural bitter terpenoids andrographolide and amarogentin.
PubMed:
Modulation of the expression of the pi class of glutathione S-transferase by Andrographis paniculata extracts and andrographolide.
PubMed:
Infrared-metabolomics approach in detecting changes in Andrographis paniculata metabolites due to different harvesting ages and times.
PubMed:
Separation of andrographolide and neoandrographolide from the leaves of Andrographis paniculata using high-speed counter-current chromatography.
PubMed:
Determination of andrograpolide sodium bisulphite in Beagle dog plasma by LC-MS/MS and its application to pharmacokinetics.
PubMed:
Anti-inflammatory effects of 27 selected terpenoid compounds tested through modulating Th1/Th2 cytokine secretion profiles using murine primary splenocytes.
PubMed:
Highly efficient and regioselective acylation of pharmacologically interesting cordycepin catalyzed by lipase in the eco-friendly solvent 2-methyltetrahydrofuran.
PubMed:
Anti-inflammatory activity of new compounds from Andrographis paniculata by NF-kappaB transactivation inhibition.
PubMed:
Absorption of andrographolides from Andrographis paniculata and its effect on CCl(4)-induced oxidative stress in rats.
PubMed:
Analysis of urinary andrographolides and antioxidant status after oral administration of Andrographis paniculata leaf extract in rats.