|
Category: antimicrobial agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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) |
Organoleptic Properties:
| |
| Odor and/or flavor descriptions from others (if found). |
| |
| |
Cosmetic Information:
Suppliers:
| BOC Sciences |
| For experimental / research use only. |
| D,L-1'-Acetoxychavicol acetate ≥95%
Odor: characteristic Use: D,L-1?-Acetoxychavicol acetate is first isolated from the rhizomes of ginger-like plants. It has ability to inhibit exportin 1 |
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: | 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.
|
Safety References:
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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)- |
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. |
|