| Name: | (1R,2R,4aS,8aS)-1-(3-hydroxy-3-methylpent-4-enyl)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol |
| CAS Number: | 4630-08-4 |
|
| FDA UNII: | A1A2FI1KEJ |
| XlogP3-AA: | 4.90 (est) |
| Molecular Weight: | 308.50532000 |
| Formula: | C20 H36 O2 |
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Soluble in: |
| | alcohol |
| Insoluble in: |
| | water |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
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
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| Dermal Toxicity: |
|
Not determined
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| Inhalation Toxicity: |
|
Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for (13S)-labd-14-ene-8,13-diol usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for (13S)-labd-14-ene-8,13-diol flavor usage levels up to: |
| | not for flavor use.
|
Safety References:
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| National Institute of Allergy and Infectious Diseases:Data |
| (1R,2R,4aS,8aS)-1-(3-hydroxy-3-methylpent-4-enyl)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol |
| Chemidplus:0004630084 |
References:
| | (1R,2R,4aS,8aS)-1-(3-hydroxy-3-methylpent-4-enyl)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol |
| Pubchem (sid): | 135264097 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| (1R,2R,4aS,8aS)-1-(3- | hydroxy-3-methylpent-4-enyl)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol | | (13S)- | labd-14-ene-8,13-diol |
Articles:
| PubMed:Sclareol induces plant resistance to root-knot nematode partially through ethylene-dependent enhancement of lignin accumulation. |
| PubMed:Synthesis of the Putative Structure of 15-Oxopuupehenoic Acid. |
| PubMed:Labdane diterpenoids from Salvia reuterana. |
| PubMed:A short synthetic route towards merosesquiterpenes with a benzoxanthene skeleton. |
| PubMed:Essential oil composition, antioxidant and antifungal activities of Salvia sclarea L. from Munzur Valley in Tunceli, Turkey. |
| PubMed:Characterization of two genes for the biosynthesis of abietane-type diterpenes in rosemary (Rosmarinus officinalis) glandular trichomes. |
| PubMed:[Engineering Saccharomyces cerevisiae for sclareol production]. |
| PubMed:[Preface for special issue on synthetic biology (2013)]. |
| PubMed:Sclareol reduces CD4+ CD25+ FoxP3+ Treg cells in a breast cancer model in vivo. |
| PubMed:Hh signaling inhibitors from Vitex negundo; naturally occurring inhibitors of the GLI1-DNA complex. |
| PubMed:Chemical composition and anticancer activity of essential oils of Mediterranean sage (Salvia officinalis L.) grown in different environmental conditions. |
| PubMed:Extracellular localization of the diterpene sclareol in clary sage (Salvia sclarea L., Lamiaceae). |
| PubMed:Bioactive constituents of Salvia chrysophylla Stapf. |
| PubMed:Toward a biosynthetic route to sclareol and amber odorants. |
| PubMed:Enzymatic biotransformation of terpenes as bioactive agents. |
| PubMed:A diterpene synthase from the clary sage Salvia sclarea catalyzes the cyclization of geranylgeranyl diphosphate to (8R)-hydroxy-copalyl diphosphate. |
| PubMed:Cancer cell spheroids as a model to evaluate chemotherapy protocols. |
| PubMed:Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture. |
| PubMed:Identification of natural diterpenes that inhibit bacterial wilt disease in tobacco, tomato and Arabidopsis. |
| PubMed:Sclareol exhibits anti-inflammatory activity in both lipopolysaccharide-stimulated macrophages and the λ-carrageenan-induced paw edema model. |
| PubMed:Antimicrobial evaluation of diterpenes from Copaifera langsdorffii oleoresin against periodontal anaerobic bacteria. |
| PubMed:First enantiospecific synthesis of marine sesquiterpene quinol akaol A. |
| PubMed:Four potato (Solanum tuberosum) ABCG transporters and their expression in response to abiotic factors and Phytophthora infestans infection. |
| PubMed:Synthesis of the scalarane sesterterpenoid 16-deacetoxy-12-epi-scalarafuranacetate. |
| PubMed:The labdane diterpene sclareol (labd-14-ene-8, 13-diol) induces apoptosis in human tumor cell lines and suppression of tumor growth in vivo via a p53-independent mechanism of action. |
| PubMed:Isolation, chemical, and biotransformation routes of labdane-type diterpenes. |
| PubMed:Chemical composition and antimicrobial activity of the essential oils from Cleome spinosa. |
| PubMed:Sclareol modulates the Treg intra-tumoral infiltrated cell and inhibits tumor growth in vivo. |
| PubMed:Mitochondria-targeted liposomes improve the apoptotic and cytotoxic action of sclareol. |
| PubMed:Hemisynthesis of two marine cheilanthane sesterterpenes from (-)-sclareol: first enantioselective synthesis of petrosaspongiolide R. |
| PubMed:Fragrance material review on sclareol. |
| PubMed:Diversity of essential oil glands of clary sage (Salvia sclarea L., Lamiaceae). |
| PubMed:Microbial hydroxylation of sclareol by Rhizopus stolonifer. |
| PubMed:Cell growth inhibitory action of an unusual labdane diterpene, 13-epi-sclareol in breast and uterine cancers in vitro. |
| PubMed:Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products. |
| PubMed:Diels-Alder cycloaddition approach to puupehenone-related metabolites: synthesis of the potent angiogenesis inhibitor 8-epipuupehedione. |
| PubMed:Liposomes modify the subcellular distribution of sclareol uptake by HCT-116 cancer cell lines. |
| PubMed:Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice. |
| PubMed:Structure elucidation and antibacterial activity of new fungal metabolites of sclareol. |
| PubMed:Calorimetric study on the induction of interdigitated phase in hydrated DPPC bilayers by bioactive labdanes and correlation to their liposome stability: The role of chemical structure. |
| PubMed:Hemisynthesis of new labdane derivatives from (-)-sclareol. |
| PubMed:Synthesis of ent-thallusin. |
| PubMed:A new route toward 7-Oxo-13-hydroxy-8,11,13-podocarpatrienes from labdane diterpenes. |
| PubMed:Labd-14-ene-8,13-diol (sclareol) induces cell cycle arrest and apoptosis in human breast cancer cells and enhances the activity of anticancer drugs. |
| PubMed:Cytotoxic and antitumor activity of liposome-incorporated sclareol against cancer cell lines and human colon cancer xenografts. |
| PubMed:NpPDR1, a pleiotropic drug resistance-type ATP-binding cassette transporter from Nicotiana plumbaginifolia, plays a major role in plant pathogen defense. |
| PubMed:First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol. |
| PubMed:A comparative study of the effects of cholesterol and sclareol, a bioactive labdane type diterpene, on phospholipid bilayers. |
| PubMed:Effect of 13-epi-sclareol on the bacterial respiratory chain. |
| PubMed:Pathogen-responsive expression of a putative ATP-binding cassette transporter gene conferring resistance to the diterpenoid sclareol is regulated by multiple defense signaling pathways in Arabidopsis. |
| PubMed:Identification of regulatory sequence elements within the transcription promoter region of NpABC1, a gene encoding a plant ABC transporter induced by diterpenes. |
| PubMed:Antibacterial diterpenoids from Astragalus brachystachys. |
| PubMed:The plant PDR family of ABC transporters. |
| PubMed:Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit. |
| PubMed:The ABC transporter SpTUR2 confers resistance to the antifungal diterpene sclareol. |
| PubMed:Chromatographic (GC-MS, HPLC) and virological evaluations of Salvia sclarea infected by BBWV-I. |
| PubMed:A plant plasma membrane ATP binding cassette-type transporter is involved in antifungal terpenoid secretion. |
| PubMed:Labdane type diterpenes down-regulate the expression of c-Myc protein, but not of Bcl-2, in human leukemia T-cells undergoing apoptosis. |
| PubMed:Biotransformation of two cytotoxic terpenes, alpha-santonin and sclareol by Botrytis cinerea. |
| PubMed:Potential nitrite scavengers as inhibitors of the formation of N-nitrosamines in solution and tobacco matrix systems. |
| PubMed:Synthesis of 11,12-epoxydrim-8,12-en-11-ol, 11,12-diacetoxydrimane, and warburganal from (-)-sclareol. |
| PubMed:Synthesis and antitumoral activities of marine ent-chromazonarol and related compounds. |
| PubMed:Chemical analysis and antimicrobial activity of the resin Ladano, of its essential oil and of the isolated compounds. |
| PubMed:The effect of sclareol on growth and cell cycle progression of human leukemic cell lines. |
| PubMed:A concise synthesis and in vitro cytotoxicity of new labdane diterpenes. |
| PubMed:A concise conversion of (-)-sclareol into (+)-coronarin E and (-)-7-epi-coronarin A |
| PubMed:[Plant anatomical and phytochemical evaluation of Salvia species]. |
| PubMed:Biorationals fromNicotiana protect cucumbers againstColletotrichum lagenarium (Pass.) ell. & halst disease development. |
| PubMed:Terpenoids from Salvia sclarea. |
| PubMed:Synthesis of manool-related labdane diterpenes as platelet aggregation inhibitors. |
| PubMed:Identification of four biliary metabolites of the diterpene sclareol in the laboratory rat. |
| PubMed:Leaf surface chemicals fromNicotiana affecting germination ofPeronospora tabacina (adam) sporangia. |
| PubMed:Hydroxylation and glucoside conjugation in the microbial metabolism of the diterpene sclareol. |
| PubMed:Microbial models of mammalian metabolism: fungal metabolism of the diterpene sclareol by Cunninghamella species. |
| PubMed:Influences of diterpene sclareol glycol on some dopamine related behavior. |
| PubMed:The effects of the diterpene sclareol glycol on seizures do not depend on central benzodiazepine receptors. |
| PubMed:The response of diterpene sclareol glycol to acute hypoxia in mice. |
| PubMed:[The effect of sclareol lactone and sclareol glycol on artificially induced lung metastases of Lewis lung carcinoma (a preliminary report)]. |
| PubMed:Measures of anxiety, retention and stress in the rat following treatment with the diterpene sclareol glycol. |
| PubMed:Diterpene sclareol glycol inhibits clonidine-induced aggressive responses in mice. |
| PubMed:Effects of the diterpene sclareol glycol on convulsive seizures. |
| PubMed:Effects of the diterpene sclareol glycol on body temperature in rats. |
| PubMed:[Study of the effect of sclareol glycol diterpene on the release of adenohypophysial hormones prolactin, somatotropin and adenocorticotrophic hormone]. |
| PubMed:[Study of the effect of sclareol glycol diterpene on the 3',5'-AMP level]. |
| PubMed:Experimental study of essential oils from two varieties of cultivated thyme, sesquiterpene Germacron and diterpene Sclareol for cholagogic and choleretic activity. |
| PubMed:[Effect of diterpene sklareol glycol on the conflict test and its correlation with diazepam]. |
| PubMed:[Effects of sklareol-glycol on pentylenetetrazole-induced convulsions and its interaction with diazepam]. |
| PubMed:BIOSYNTHESIS AND METABOLISM OF (14C)SCLAREOL. |
| PubMed:Biosynthesis of sclareol, beta-sitosterol, and oleanolic acid from mevalonic acid-2-C-14. |
| PubMed:Biosynthesis of 14C-sclareol and beta-sitosterol from 2-14C-mevalonic acid. |
| PubMed:[Sclareol, its chemical constitution and use in the synthesis of aromatic principles of amber; a review]. |
| PubMed:[Not Available]. |
|