(S)-curcumin
5-[(1S)-1,5-dimethyl-4-hexenyl]-2-methylphenol
 
Notes:
None found
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CAS Number: 97372-52-6Picture of molecule3D/inchi
Nikkaji Web: J1.452.594G
XlogP3: 5.10 (est)
Molecular Weight: 218.33954000
Formula: C15 H22 O
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
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
Boiling Point: 326.89 °C. @ 760.00 mm Hg (est)
Flash Point: 297.00 °F. TCC ( 147.20 °C. ) (est)
logP (o/w): 5.166 (est)
Soluble in:
 water, 1.45 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for (S)-curcumin usage levels up to:
 not for fragrance use.
 
Recommendation for (S)-curcumin flavor usage levels up to:
 not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Refined exposure assessment for curcumin (E 100)
View page or View pdf
Curcumin and normal functioning of joints: evaluation of a health claim pursuant to Article 13(5) of Regulation (EC) No 1924/2006
View page or View pdf
EPI System: View
AIDS Citations: Search
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Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 11156616
National Institute of Allergy and Infectious Diseases: Data
 2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]phenol
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References:
 2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]phenol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 11156616
Pubchem (sid): 162736585
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
HMDB (The Human Metabolome Database): Search
FDA Listing of Food Additive Status: View
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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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
 ginger java ginger
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Synonyms:
5-[(1S)-1,5-dimethyl-4-hexenyl]-2-methylphenol
2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]phenol
 phenol, 5-[(1S)-1,5-dimethyl-4-hexen-1-yl]-2-methyl-
(S)-xanthorrhizol
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Articles:
PubMed: Nonsteroidal anti-inflammatory drug activated gene-1 (NAG-1) modulators from natural products as anti-cancer agents.
PubMed: Chemopreventive efficacy of Aegle marmelos on murine transplantable tumors.
PubMed: In vitro activity of xanthorrhizol isolated from the rhizome of Javanese turmeric (Curcuma xanthorrhiza Roxb.) against Candida albicans biofilms.
PubMed: Xanthorrhizol induces apoptosis through ROS-mediated MAPK activation in human oral squamous cell carcinoma cells and inhibits DMBA-induced oral carcinogenesis in hamsters.
PubMed: Xanthorrhizol induced DNA fragmentation in HepG2 cells involving Bcl-2 family proteins.
PubMed: Ent-trachyloban-19-oic acid isolated from Iostephane heterophylla as a promising antibacterial agent against Streptococcus mutans biofilms.
PubMed: A short synthesis of bisabolane sesquiterpenes.
PubMed: Effect of curcumin-associated and lipid ligand-functionalized nanoliposomes on aggregation of the Alzheimer's Aβ peptide.
PubMed: An antimicrobial compound isolated from Cinnamomum iners leaves with activity against methicillin-resistant Staphylococcus aureus.
PubMed: Facile total synthesis of xanthorrhizol.
PubMed: Xanthorrhizol attenuates dextran sulfate sodium-induced colitis via the modulation of the expression of inflammatory genes in mice.
PubMed: Assessment of antiproliferative and antiplasmodial activities of five selected Apocynaceae species.
PubMed: In vitro activity of xanthorrhizol against Candida glabrata, C. guilliermondii, and C. parapsilosis biofilms.
PubMed: Evaluation of the antinociceptive activity and acute oral toxicity of standardized ethanolic extract of the rhizome of Curcuma xanthorrhiza Roxb.
PubMed: Xanthorrhizol, a natural sesquiterpenoid, induces apoptosis and growth arrest in HCT116 human colon cancer cells.
PubMed: trans-Directing ability of the amide group: enabling the enantiocontrol in the synthesis of 1,1-dicarboxy cyclopropanes. Reaction development, scope, and synthetic applications.
PubMed: Estrogenic activity of xanthorrhizol isolated from curcuma xanthorrhiza ROXB.
PubMed: Kanokonyl acetate-rich Indian valerian from northwestern Himalaya.
PubMed: Synergistic anticandidal activity of xanthorrhizol in combination with ketoconazole or amphotericin B.
PubMed: The effect of xanthorrhizol on the expression of matrix metalloproteinase-1 and type-I procollagen in ultraviolet-irradiated human skin fibroblasts.
PubMed: Antiproliferative property and apoptotic effect of xanthorrhizol on MDA-MB-231 breast cancer cells.
PubMed: Antibacterial activity of xanthorrhizol isolated from Curcuma xanthorrhiza Roxb. against foodborne pathogens.
PubMed: Inhibitory effect of compounds from Zingiberaceae species on human platelet aggregation.
PubMed: Development and validation of a liquid chromatography method for quantification of xanthorrhizol in roots of Iostephane heterophylla (Cav.) Benth ex Hemsl.
PubMed: Regulation of p53-, Bcl-2- and caspase-dependent signaling pathway in xanthorrhizol-induced apoptosis of HepG2 hepatoma cells.
PubMed: In vitro anti-Malassezia activity of xanthorrhizol isolated from Curcuma xanthorrhiza Roxb.
PubMed: Xanthorrhizol inhibits 12-O-tetradecanoylphorbol-13-acetate-induced acute inflammation and two-stage mouse skin carcinogenesis by blocking the expression of ornithine decarboxylase, cyclooxygenase-2 and inducible nitric oxide synthase through mitogen-activated protein kinases and/or the nuclear factor-kappa B.
PubMed: Xanthorrhizol exhibits antiproliferative activity on MCF-7 breast cancer cells via apoptosis induction.
PubMed: Effect of coating the wells of a polystyrene microtiter plate with xanthorrhizol on the biofilm formation of Streptococcus mutans.
PubMed: In vitro activity of xanthorrhizol against Streptococcus mutans biofilms.
PubMed: Chemical composition and anti-mosquito potential of rhizome extract and volatile oil derived from Curcuma aromatica against Aedes aegypti (Diptera: Culicidae).
PubMed: Antioxidant and antiinflammatory activities of xanthorrhizol in hippocampal neurons and primary cultured microglia.
PubMed: Xanthorrhizol induces apoptosis via the up-regulation of bax and p53 in HeLa cells.
PubMed: Inhibitory effects of compounds from Zingiberaceae species on platelet activating factor receptor binding.
PubMed: Xanthorrhizol has a potential to attenuate the high dose cisplatin-induced nephrotoxicity in mice.
PubMed: Xanthorrhizol, a natural sesquiterpenoid from Curcuma xanthorrhiza, has an anti-metastatic potential in experimental mouse lung metastasis model.
PubMed: Phosphorylation of c-Jun N-terminal Kinases (JNKs) is involved in the preventive effect of xanthorrhizol on cisplatin-induced hepatotoxicity.
PubMed: Abrogation of cisplatin-induced hepatotoxicity in mice by xanthorrhizol is related to its effect on the regulation of gene transcription.
PubMed: Suppressive effect of natural sesquiterpenoids on inducible cyclooxygenase (COX-2) and nitric oxide synthase (iNOS) activity in mouse macrophage cells.
PubMed: Biological and mechanistic activities of xanthorrizol and 4-(1',5'-dimethylhex-4'-enyl)-2-methylphenol isolated from Iostephane heterophylla.
PubMed: Antibacterial activity of xanthorrhizol from Curcuma xanthorrhiza against oral pathogens.
PubMed: Xanthorrhizol: a potential antibacterial agent from Curcuma xanthorrhiza against Streptococcus mutans.
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