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
 
Notes:
a phytogenic antineoplastic agent; activates caspase 8 and induces apoptosis.
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(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one (Click)
CAS Number: 5508-58-7Picture of molecule
ECHA EINECS - REACH Pre-Reg: 226-852-5
FDA UNII: 410105JHGR
Nikkaji Web: J3.154.642G
Beilstein Number: 0042762
MDL: MFCD07778082
XlogP3-AA: 2.20 (est)
Molecular Weight: 350.45510000
Formula: C20 H30 O5
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic ingredient for skin conditioning
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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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)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: skin conditioning
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Suppliers:
Changsha Organic Herb
Andrographis Paniculata Extract
Coompo
For experimental / research use only.
Andrographolide from Plants ≥96%
Odor: characteristic
Use: Andrographolide is a labdane diterpenoid that shown anti-inflammatory, immuno- suppressant and neuroprotective effects, andrographolide is used experimentally in different areas of research, including Cell signaling, immunomodulation and stroke.
ExtraSynthese
For experimental / research use only.
Andrographolide (HPLC) ≥95%
Santa Cruz Biotechnology
For experimental / research use only.
Andrographolide ≥98%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Andrographolide 98%
TCI AMERICA
For experimental / research use only.
Andrographolide >98.0%(HPLC)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50  11460 mg/kg
Indian Journal of Medical Research. Vol. 92, Pg. 276, 1990.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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.
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Safety References:
EPI System: View
ClinicalTrials.gov: search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5318517
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
Chemidplus: 0005508587
RTECS: LU3490750 for cas# 5508-58-7
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References:
 (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5318517
Pubchem (sid): 135023123
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C20214
HMDB (The Human Metabolome Database): Search
Export Tariff Code: 2932.20.5050
Household Products: Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
EFSA Update of results on the monitoring of furan levels in food: Read Report
EFSA Previous report: Results on the monitoring of furan levels in food: Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food: Read Report
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 andrographis paniculata leaves
Search Trop  Picture
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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)-6hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
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Articles:
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.
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