EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes

curcumol
6H-3a,6-epoxyazulen-6-ol, octahydro-3-methyl-8-methylene-5-(1-methylethyl)-, (3S,5S,6S,8aS)-

Supplier Sponsors

Name:(2S,5S,8S,9S)-9-isopropyl-2-methyl-6-methylene-11-oxatricyclo[6.2.1.01,5]undecan-8-ol
CAS Number: 4871-97-0Picture of molecule3D/inchi
FDA UNII: 9190RTN07X
MDL:MFCD00272163
XlogP3-AA:2.80 (est)
Molecular Weight:236.35468000
Formula:C15 H24 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 80.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 332.00 to 334.00 °C. @ 760.00 mm Hg (est)
Flash Point: 274.00 °F. TCC ( 134.70 °C. ) (est)
logP (o/w): 3.276 (est)
Soluble in:
 water, 59.2 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Curcumol 98%
BOC Sciences
For experimental / research use only.
Curcumol >98%
Odor: characteristic
Use: Curcumol is a pure monomer isolated from Rhizoma Curcumaeis with antitumor activities.
Coompo
For experimental / research use only.
Curcumol from Plants ≥98%
Odor: characteristic
Use: Curcumol is a common traditional Chinese medicine with antitumor activities. Curcumol is one of the representative index components in the quality standard of the essential oil which is currently used as an anti-cancer and anti-virus remedy,and embodied in the Pharmacopoeia of the P.R.China(2005). Curcumol induced a rapid translocation of Bax from cytosol into mitochondria within 6 h, leading to a rapid dissipation of mitochondrial membrane potential (??m), implying that mitochondria play an important role in the curcumol-induced apoptosis. The fact that Z-VAD-fmk, a broad-spectrum inhibitor of caspases, did not reduce the curcumol-induced apoptosis showed that caspases were not involved in curcumol-induced apoptosis, which was further verified by monitoring the caspase-3 activation inside living cells stably expressing SCAT3, a FRET plasmid. curcumol induced cell death in a dominant apoptotic fashion via the caspases-independent mitochondrial pathway in ASTC-a-1 cells.
Sigma-Aldrich
For experimental / research use only.
( -)-Curcumol
analytical standard
 
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
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for curcumol usage levels up to:
 not for fragrance use.
 
Recommendation for curcumol flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :160771
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2S,5S,8S,9S)-9-isopropyl-2-methyl-6-methylene-11-oxatricyclo[6.2.1.01,5]undecan-8-ol
Chemidplus:0004871970
 
References:
 (2S,5S,8S,9S)-9-isopropyl-2-methyl-6-methylene-11-oxatricyclo[6.2.1.01,5]undecan-8-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):160771
Pubchem (sid):135116564
 
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):HMDB38122
FooDB:FDB017348
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 turmeric rhizome
Search Trop Picture
 turmeric wild turmeric
Search Trop Picture
 
Synonyms:
6H-3a,6-epoxyazulen-6-ol, octahydro-3-methyl-8-methylene-5-(1-methylethyl)-, (3S,5S,6S,8aS)-
(3S-(3alpha,3aalpha,5alpha,6alpha,8abeta))-octahydro-3-methyl-8-methylene-5-(1-methyl ethyl)-6H-3a,6-epoxyazulen-6-ol
(2S,5S,8S,9S)-9-isopropyl-2-methyl-6-methylene-11-oxatricyclo[6.2.1.01,5]undecan-8-ol
 

Articles:

PubMed:Analysis and pharmacokinetic study of curdione in Rhizoma Curcumae by UPLC/QTOF/MS.
PubMed:Identification of CYP2C19 inhibitors from phytochemicals using the recombinant human enzyme model.
PubMed:Curcumol suppresses RANKL-induced osteoclast formation by attenuating the JNK signaling pathway.
PubMed:Pharmacokinetics and liver distribution study of unbound curdione and curcumol in rats by microdialysis coupled with rapid resolution liquid chromatography (RRLC) and tandem mass spectrometry.
PubMed:Curcumol from Rhizoma Curcumae suppresses epileptic seizure by facilitation of GABA(A) receptors.
PubMed:Curcumol exhibits anti-inflammatory properties by interfering with the JNK-mediated AP-1 pathway in lipopolysaccharide-activated RAW264.7 cells.
PubMed:Synthesis, anti-tumor activity, and structure-activity relationships of curcumol derivatives.
PubMed:[Mechanism study on anti-proliferative effects of curcumol in human hepatocarcinoma HepG2 cells].
PubMed:Zedoary oil (Ezhu You) inhibits proliferation of AGS cells.
PubMed:Modeling anti-allergic natural compounds by molecular topology.
PubMed:[Effects end mechanisms of curcumol beta-cyclodextrin compound on the proliferation and apoptosls of esophageal carcinoma cell line TE-1].
PubMed:Microbial transformation of curcumol by Aspergillus niger.
PubMed:[Effect and mechanism of curcumol on angiogenesis activity of zebrafishes].
PubMed:[Analysis of volatile compounds from Curcuma by microwave assisted solid phase headspace-gas chromatography].
PubMed:Subunit-specific inhibition of glycine receptors by curcumol.
PubMed:Anti-cancer properties of terpenoids isolated from Rhizoma Curcumae--a review.
PubMed:Inhibitory Effect of Curcumol on Jak2-STAT Signal Pathway Molecules of Fibroblast-Like Synoviocytes in Patients with Rheumatoid Arthritis.
PubMed:[Effect of curcumol on proliferation and apoptosis of nasopharyngeal carcinoma cell line CNE-2].
PubMed:[Comparison of content of curdione, curcumol, germacrone and beta-elemene in different varieties of vinegar backed Rhizoma Curcuma].
PubMed:Isolation and identification of phase 1 metabolites of curcumol in rats.
PubMed:[HPLC determination of six components in zedoary turmeric oil and its related injections].
PubMed:Preparative isolation and purification of six volatile compounds from essential oil of Curcuma wenyujin using high-performance centrifugal partition chromatography.
PubMed:Curcumol induces apoptosis via caspases-independent mitochondrial pathway in human lung adenocarcinoma ASTC-a-1 cells.
PubMed:Determination of curcumol in rat plasma by capillary gas chromatography with a hydrogen flame ionization detector.
PubMed:Chemical constituents from the radix of Curcuma wenyujin.
PubMed:Qualitative and quantitative analysis of four species of Curcuma rhizomes using twice development thin layer chromatography.
PubMed:A new eudesmane sesquiterpene lactone from Curcuma wenyujin.
PubMed:[Determination of curcumol in plasma by HPLC-MS/MS method and its pharmacokinetics in Beagle dogs].
PubMed:Microbial transformation of curcumol by Cunninghamella blakesleana.
PubMed:Four novel metabolites from microbial transformation of curcumol by Cunninghamella blakesleana.
PubMed:[Study on the chemical constituents of Curcuma phaeocaulis].
PubMed:Simultaneous determination of 11 characteristic components in three species of Curcuma rhizomes using pressurized liquid extraction and high-performance liquid chromatography.
PubMed:Optimization of GC-MS conditions based on resolution and stability of analytes for simultaneous determination of nine sesquiterpenoids in three species of Curcuma rhizomes.
PubMed:[Determination of curcumol in Rhizoma Curcumae by GC].
PubMed:Fast determination of curcumol, curdione and germacrone in three species of Curcuma rhizomes by microwave-assisted extraction followed by headspace solid-phase microextraction and gas chromatography-mass spectrometry.
PubMed:Seasonal variation and analgesic properties of different parts from Curcuma zedoaria Roscoe (Zingiberaceae) grown in Brazil.
PubMed:[The fingerprint of Ezhu by GC-MS].
PubMed:Effects of different ingredients of zedoary on gene expression of HSC-T6 cells.
PubMed:Molecular genetic and chemical assessment of Rhizoma Curcumae in China.
PubMed:Identification and quantitation of eleven sesquiterpenes in three species of Curcuma rhizomes by pressurized liquid extraction and gas chromatography-mass spectrometry.
PubMed:[Absorption of zedoary oil in rat intestine using in situ single pass perfusion model].
PubMed:A new triterpenoid from Entodon okamurae Broth.
PubMed:[Studies on chemical constituents of Curcuma aromatica salisb].
PubMed:[Synthesis of 11-aminomethyl-2,6-dimethyl-3,9-diisopropyl-tricyclo [5.3.2.0(1.5)] dodeca-5,9-dien-8-ol].
PubMed:The absolute stereostructure of curcumol isolated from Curcuma wenyujin.
PubMed:[The metabolism of 3H-curcumol in normal rats and tumour bearing mice (author's transl)].
PubMed:[The determination of curcumol in the volatile oil of Curcuma aromatica by phloroglucinol spectrophotometry (author's transl)].
PubMed:[Determination of curcumol in the volatile oil of Curcuma aromatica (author's transl)].
PubMed:Structure of curcumol.
PubMed:Structure of curcumol.
 
Notes:
Constit. of Curcuma zedoaria (zedoary)
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