galangal acetate
(aS)-4-(acetyloxy)-a-ethenylbenzenemethanol
 
Notes:
antifungal component of alpinia galanga. Constit. of Alpinia galanga (greater galangal) Constit. of Acorus calamus (sweet flag) Constit. of Alpinia galanga (greater galangal)
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(1S)-1-(4-acetoxyphenyl)-2-propen-1-yl acetate (Click)
CAS Number: 52946-22-2Picture of molecule
FDA UNII: SQV3080A20
Nikkaji Web: J592.628I
MDL: MFCD01632488
XlogP3-AA: 2.20 (est)
Molecular Weight: 234.25138000
Formula: C13 H14 O4
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: antimicrobial agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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IBM Patents: Obtain
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 325.40 °C. @ 760.00 mm Hg (est)
Flash Point: 316.00 °F. TCC ( 157.80 °C. ) (est)
logP (o/w): 1.900 (est)
Soluble in:
 water, 233.4 mg/L @ 25 °C (est)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antimicrobial agents
antiseborrhoeic agents
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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: antimicrobial agents
Recommendation for galangal acetate usage levels up to:
 not for fragrance use.
 
Recommendation for galangal acetate flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 400072
National Institute of Allergy and Infectious Diseases: Data
 (1S)-1-(4-acetoxyphenyl)-2-propen-1-yl acetate
Chemidplus: 0052946222
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References:
 (1S)-1-(4-acetoxyphenyl)-2-propen-1-yl acetate
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 400072
Pubchem (sid): 35561595
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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
CHEMBL: View
KEGG (GenomeNet): C10426
HMDB (The Human Metabolome Database): HMDB41006
FooDB: FDB020866
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: 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
 galangal
Search Trop  Picture
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Synonyms:
1'-acetoxychavicol acetate
(1S)-1-(4-acetoxyphenyl)-2-propen-1-yl acetate
(alpha)-4-(acetyl oxy)-alpha-ethenyl benzene methanol
(aS)-4-(acetyloxy)-a-ethenylbenzenemethanol
 benzenemethanol, 4-(acetyloxy)-a-ethenyl-, acetate, (aS)-
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Articles:
US Patents: 6,504,048 - Flavorant compositions
PubMed: Effect of Pakistani medicinal plants on IgE/antigen- and ionophore-induced mucosal mast cells degranulation.
PubMed: Evaluating the anti Mycobacterium tuberculosis activity of Alpinia galanga (L.) Willd. axenically under reducing oxygen conditions and in intracellular assays.
PubMed: Isolation, synthesis and biological evaluation of phenylpropanoids from the rhizomes of Alpania galanga.
PubMed: The synergistic effect of 1'-acetoxychavicol acetate and sodium butyrate on the death of human hepatocellular carcinoma cells.
PubMed: MicroRNAs contribute to the anticancer effect of 1'-acetoxychavicol acetate in human head and neck squamous cell carcinoma cell line HN4.
PubMed: 1'-Acetoxychavicol acetate promotes caspase 3-activated glioblastoma cell death by overcoming enhanced cytokine expression.
PubMed: AMPK synergizes with the combined treatment of 1'-acetoxychavicol acetate and sodium butyrate to upregulate phase II detoxifying enzyme activities.
PubMed: 1'-Acetoxychavicol acetate isolated from Alpinia galanga ameliorates ovalbumin-induced asthma in mice.
PubMed: Antimicrobial compounds from Alpinia conchigera.
PubMed: 1'-acetoxychavicol acetate inhibits adipogenesis in 3T3-L1 adipocytes and in high fat-fed rats.
PubMed: 1'-Acetoxychavicol acetate inhibits growth of human oral carcinoma xenograft in mice and potentiates cisplatin effect via proinflammatory microenvironment alterations.
PubMed: Alterations of microRNA expression patterns in human cervical carcinoma cells (Ca Ski) toward 1'S-1'-acetoxychavicol acetate and cisplatin.
PubMed: Agrobacterium-mediated transformation in Alpinia galanga (Linn.) Willd. for enhanced acetoxychavicol acetate production.
PubMed: Phenylpropanoids of Alpinia galanga as efflux pump inhibitors in Mycobacterium smegmatis mc² 155.
PubMed: Effects of the tropical ginger compound,1'-acetoxychavicol acetate, against tumor promotion in K5.Stat3C transgenic mice.
PubMed: Nuclear export of proteins and drug resistance in cancer.
PubMed: Cancer cell signaling pathways targeted by spice-derived nutraceuticals.
PubMed: Direct and indirect organogenesis of Alpinia galanga and the phytochemical analysis.
PubMed: 1'-Acetoxychavicol acetate enhances the phase II enzyme activities via the increase in intranuclear Nrf2 level and cytosolic p21 level.
PubMed: Biological activity of water-soluble inclusion complexes of 1'-acetoxychavicol acetate with cyclodextrins.
PubMed: 1'-Acetoxychavicol acetate suppresses angiogenesis-mediated human prostate tumor growth by targeting VEGF-mediated Src-FAK-Rho GTPase-signaling pathway.
PubMed: Anti-influenza viral effects of novel nuclear export inhibitors from Valerianae Radix and Alpinia galanga.
PubMed: The apoptotic effect of 1's-1'-acetoxychavicol acetate from Alpinia conchigera on human cancer cells.
PubMed: Antileishmanial phenylpropanoids from Alpinia galanga (Linn.) Willd.
PubMed: 1'S-1'-acetoxyeugenol acetate: a new chemotherapeutic natural compound against MCF-7 human breast cancer cells.
PubMed: Galangal pungent component, 1'-acetoxychavicol acetate, activates TRPA1.
PubMed: Effects of ATRA combined with citrus and ginger-derived compounds in human SCC xenografts.
PubMed: Antibacterial activity of Thai herbal extracts on acne involved microorganism.
PubMed: Comparison of glutathione reductase activity and the intracellular glutathione reducing effects of 13 derivatives of 1'-acetoxychavicol acetate in Ehrlich ascites tumor cells.
PubMed: Halogenated analogs of 1'-acetoxychavicol acetate, Rev-export inhibitor from Alpinia galanga, designed from mechanism of action.
PubMed: Antiplasmid activity of 1'-acetoxychavicol acetate from Alpinia galanga against multi-drug resistant bacteria.
PubMed: Acetoxybenzhydrols as highly active and stable analogues of 1'S-1'-acetoxychavicol, a potent antiallergic principal from Alpinia galanga.
PubMed: New Rev-export inhibitor from Alpinia galanga and structure-activity relationship.
PubMed: Identification of dihydrogalangal acetate in galangal [Alpinia galangal (L.) Swartz] extracts.
PubMed: Effect of naturally occurring hydroxychavicol acetate on the cytokine production in T helper cells.
PubMed: Structural development of benzhydrol-type 1'-acetoxychavicol acetate (ACA) analogs as human leukemia cell-growth inhibitors based on quantitative structure-activity relationship (QSAR) analysis.
PubMed: Citrus nobiletin suppresses bone loss in ovariectomized ddY mice and collagen-induced arthritis in DBA/1J mice: possible involvement of receptor activator of NF-kappaB ligand (RANKL)-induced osteoclastogenesis regulation.
PubMed: (1'S)-Acetoxychavicol acetate and its enantiomer inhibit tumor cells proliferation via different mechanisms.
PubMed: 1'-Acetoxychavicol acetate-induced cytotoxicity is accompanied by a rapid and drastic modulation of glutathione metabolism.
PubMed: Structure-activity relationships of 1'-acetoxychavicol acetate homologues as new nuclear export signal inhibitors.
PubMed: Targeting NOX, INOS and COX-2 in inflammatory cells: chemoprevention using food phytochemicals.
PubMed: Pro-apoptotic effects of 1'-acetoxychavicol acetate in human breast carcinoma cells.
PubMed: Cytotoxicity, apoptosis and DNA damage induced by Alpinia galanga rhizome extract.
PubMed: The sulphorhodamine (SRB) assay and other approaches to testing plant extracts and derived compounds for activities related to reputed anticancer activity.
PubMed: Inhibitory activity of Thai condiments on pandemic strain of Vibrio parahaemolyticus.
PubMed: Cellular thiol status-dependent inhibition of tumor cell growth via modulation of p27(kip1) translocation and retinoblastoma protein phosphorylation by 1'-acetoxychavicol acetate.
PubMed: 1'S-1'-acetoxychavicol acetate isolated from Alpinia galanga inhibits human immunodeficiency virus type 1 replication by blocking Rev transport.
PubMed: Cancer-preventive anti-oxidants that attenuate free radical generation by inflammatory cells.
PubMed: 1'-Acetoxychavicol acetate inhibits RANKL-induced osteoclastic differentiation of RAW 264.7 monocytic cells by suppressing nuclear factor-kappaB activation.
PubMed: Zingiberaceous and citrus constituents, 1'-acetoxychavicol acetate, zerumbone, auraptene, and nobiletin, suppress lipopolysaccharide-induced cyclooxygenase-2 expression in RAW264.7 murine macrophages through different modes of action.
PubMed: 1'-Acetoxychavicol acetate induces apoptosis of myeloma cells via induction of TRAIL.
PubMed: Lipase-catalyzed preparation of optically active 1'-acetoxychavicol acetates and their structure-activity relationships in apoptotic activity against human leukemia HL-60 cells.
PubMed: Inhibitors of nitric oxide production from the rhizomes of Alpinia galanga: structures of new 8-9' linked neolignans and sesquineolignan.
PubMed: Identification of a novel blocker of I kappa B alpha kinase that enhances cellular apoptosis and inhibits cellular invasion through suppression of NF-kappa B-regulated gene products.
PubMed: 1'-acetoxychavicol acetate is a novel nuclear factor kappaB inhibitor with significant activity against multiple myeloma in vitro and in vivo.
PubMed: Cytotoxicity of plants from Malaysia and Thailand used traditionally to treat cancer.
PubMed: 1'S-1'-Acetoxychavicol acetate as a new type inhibitor of interferon-beta production in lipopolysaccharide-activated mouse peritoneal macrophages.
PubMed: Structure-activity relationships of 1'S-1'-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages.
PubMed: Inhibition of cell proliferation by nobiletin, a dietary phytochemical, associated with apoptosis and characteristic gene expression, but lack of effect on early rat hepatocarcinogenesis in vivo.
PubMed: Modifying effects of 1'-acetoxychavicol acetate (ACA) and the novel synthetic retinoids Re-80, Am-580 and Am-55P in a two-stage carcinogenesis model in female rats.
PubMed: Induction of apoptosis in human myeloid leukemic cells by 1'-acetoxychavicol acetate through a mitochondrial- and Fas-mediated dual mechanism.
PubMed: Rapid analysis of gene expression changes caused by liver carcinogens and chemopreventive agents using a newly developed three-dimensional microarray system.
PubMed: Antiallergic principles from Alpinia galanga: structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-alpha and IL-4 in RBL-2H3 cells.
PubMed: Gastroprotective effects of phenylpropanoids from the rhizomes of Alpinia galanga in rats: structural requirements and mode of action.
PubMed: Effects of selected food factors with chemopreventive properties on combined lipopolysaccharide- and interferon-gamma-induced IkappaB degradation in RAW264.7 macrophages.
PubMed: Further investigation of the modifying effect of various chemopreventive agents on apoptosis and cell proliferation in human colon cancer cells.
PubMed: Involvement of protein tyrosine phosphorylation and reduction of cellular sulfhydryl groups in cell death induced by 1' -acetoxychavicol acetate in Ehrlich ascites tumor cells.
PubMed: Cell proliferation in cancer prevention; effects of preventive agents on estrogen-related endometrial carcinogenesis model and on an in vitro model in human colorectal cells.
PubMed: Apoptosis induced by 1'-acetoxychavicol acetate in Ehrlich ascites tumor cells is associated with modulation of polyamine metabolism and caspase-3 activation.
PubMed: Inhibitory effects of 1'-acetoxychavicol acetate on N-Nitrosobis(2-oxopropyl)-amine-induced initiation of cholangiocarcinogenesis in Syrian hamsters.
PubMed: Structure-activity relationships of (1'S)-1'-acetoxychavicol acetate, a major constituent of a southeast Asian condiment plant Languas galanga, on the inhibition of tumor-promoter-induced Epstein-Barr virus activation.
PubMed: Suppression of N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis by dietary feeding of 1'-acetoxychavicol acetate.
PubMed: Pungent principal of Alpinia galangal (L.) swartz and its applications.
PubMed: Suppression of tumor promoter-induced oxidative stress and inflammatory responses in mouse skin by a superoxide generation inhibitor 1'-acetoxychavicol acetate.
PubMed: Prevention by 1'-acetoxychavicol acetate of the induction but not growth of putative preneoplastic, glutathione S-transferase placental form-positive, focal lesions in the livers of rats fed a choline-deficient, L-amino acid-defined diet.
PubMed: Inhibition by 1'-acetoxychavicol acetate of lipopolysaccharide- and interferon-gamma-induced nitric oxide production through suppression of inducible nitric oxide synthase gene expression in RAW264 cells.
PubMed: Chemoprevention of azoxymethane-induced rat colon carcinogenesis by a xanthine oxidase inhibitor, 1'-acetoxychavicol acetate.
PubMed: A xanthine oxidase inhibitor 1'-acetoxychavicol acetate inhibits azoxymethane-induced colonic aberrant crypt foci in rats.
PubMed: 1'-Acetoxychavicol acetate, a superoxide anion generation inhibitor, potently inhibits tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in ICR mouse skin.
PubMed: Chemopreventive effect of a xanthine oxidase inhibitor, 1'-acetoxychavicol acetate, on rat oral carcinogenesis.
PubMed: 1'-Acetoxychavicol acetate as an inhibitor of phagocytosis of macrophages.
PubMed: Possible anti-tumour promoting properties of traditional Thai food items and some of their active constituents.
PubMed: Acetoxychavicol Acetate, an Antifungal Component of Alpinia galanga1.
PubMed: Acetoxychavicol acetate, an antifungal component of Alpinia galanga.
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