(13S)-labd-14-ene-8,13-diol
(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
 
Notes:
None found
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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
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 alcohol
Insoluble in:
 water
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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 (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.
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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
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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
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Other Information:
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
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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
 found in nature
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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
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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].
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