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

CAS: 5508-58-7 C20 H30 O5 MW: 350.45510000

Identification

Nameandrographolide
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 Number5508-58-7
EINECS226-852-5
FDA UNII410105JHGR
Molecular FormulaC20 H30 O5
Molecular Weight350.45510000
MDL NumberMFCD07778082
Nikkaji NumberJ3.154.642G
Beilstein0042762

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

CosIngcosmetic data
Cosmetic Usesskin conditioning

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 11460 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycosmetic ingredient for skin conditioning
Recommendation for andrographolide usage levels up tonot for fragrance use.
Recommendation for andrographolide flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

andrographis paniculata leaves

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.