(1R,2R,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol

C20 H36 O2 MW: 308.50532000 balsamic woody

Identification

Namesclareol
IUPAC(1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
EINECS208-194-0
FDA UNIISearch
Molecular FormulaC20 H36 O2
Molecular Weight308.50532000
MDL NumberMFCD00869558
Nikkaji NumberJ971.072H
Beilstein2054148
CoE Number10311

Regulatory

JECFA Food Flavoring2029 (-)-sclareol
DG SANTE Food Flavourings02.206 (-)-sclareol
FEMA Number4502
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)515-03-7 ; (-)-SCLAREOL

Physical Properties

Appearance amber solid (est)
Assay 98.00 to 100.00 sum of isomers
Food Chemicals Codex Listed No
Melting Point 105.00 to 107.00 °C. @ 760.00 mm Hg
Boiling Point 218.00 to 220.00 °C. @ 19.00 mm Hg
Flash Point 336.00 °F. TCC ( 169.10 °C. ) (est)
logP (o/w) 5.233 (est)
Soluble in alcohol

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesperfuming agents

Organoleptic Properties

Odor Strength low
Substantivity 292 hour(s) at 100.00 %
Odor Description at 100.00 %.
Odor sample from RJR Technical Company
Taste Description sweet woody balsamic clary sage amber weedy brothy cascarilla

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-rat LD50 > 5000 mg/kg
Dermal Toxicityskin-rabbit LD50 > 5000 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
IFRA Critical EffectDermal sensitization
IFRA Purity Specification98% minimum purity
fragrance material specificationSclareol used as a fragrance ingredient should have a minimum purity of 98%.
maximum skin levels for fine fragrances0.0200 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey). (IFRA, 2004)
Recommendation for sclareol usage levels up to4.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics0.0300 %
Dermal Systemic Exposure in Cosmetic Products0.0008 mg/kg/day (IFRA, 2004)
Maximised Survey-derived Daily Intakes (MSDI-EU)0.67 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI)3900 (μg/person/day)
Threshold of Concern1800 (μg/person/day)
Structure ClassI
baked goods10.00000
beverages(nonalcoholic)5.00000
beverages(alcoholic)5.00000
breakfast cereal5.00000
cheese7.00000
chewing gum-
condiments / relishes20.00000
confectionery froastings10.00000
egg products-
fats / oils5.00000
fish products2.00000
frozen dairy7.00000
fruit ices10.00000
gelatins / puddings10.00000
granulated sugar-
gravies5.00000
hard candy10.00000
imitation dairy7.00000
instant coffee / tea5.00000
jams / jellies7.00000
meat products2.00000
milk products7.00000
nut products5.00000
other grains5.00000
poultry2.00000
processed fruits7.00000
processed vegetables7.00000
reconstituted vegetables7.00000
seasonings / flavors5.00000
snack foods10.00000
soft candy10.00000
soups5.00000
sugar substitutes-
sweet sauces5.00000
Dairy products, excluding products of category 02.0 (01.0)7.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0)5.00000
Edible ices, including sherbet and sorbet (03.0)10.00000
Processed fruit (04.1)7.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2)-
Confectionery (05.0)10.00000
Chewing gum (05.3)-
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0)5.00000
Bakery wares (07.0)10.00000
Meat and meat products, including poultry and game (08.0)2.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0)2.00000
Eggs and egg products (10.0)-
Sweeteners, including honey (11.0)-
Salts, spices, soups, sauces, salads, protein products, etc. (12.0)5.00000
Foodstuffs intended for particular nutritional uses (13.0)10.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1)5.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2)10.00000
Ready-to-eat savouries (15.0)20.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0)5.00000

Beijing Lys Chemicals Co, LTD.

From Grams to Tons

Fine chemical high-tech company which contains R&D, production, and sales.

View All Website 86-10-68418738 jiayanyong@lyschem.com

Berje Inc.

Where the world comes to its senses

Where the world comes to its senses - Berjé is a global distributor of Essential Oils and Aromatic Chemicals.

View All Website 973-748-8980 tlauzurica@berjeinc.com

BOC Sciences

Best of Chemicals Supplier

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Fleurchem, Inc.

Have A Flavorful Day

A leading global manufacturer and supplier of ingredients for Flavors, Fragrances, AromaTherapy, Foods, Beverages, Personal Care Products, and other uses.

View All Website 845-341-2100 info@fleurchem.com

Foreverest Resources Ltd.

Leading pine based chemicals supplier

Supplying turpentine based and natural/extracted flavor & fragrance ingredients.

View All Website +86 (0)592 5105533 info@foreverest.cn

H. Interdonati, Inc.

Innovative products

Because your flavors and fragrances are only as good as their source "Since 1952"

View All Website 800 367-6617 flavorplus@hinterdonati.com

Indukern, S.A. F&F Ingredients Division

Commitment to quality

Idukern F&F Ingredients is your partner for the fragrance and flavor ingredients.

View All Website +34 93 506 91 00 info@indukern.es

Lluch Essence S.L.

A family company dedicated to sales and distribution

Flexibility, availability, price and quality.

View All Website 34 93 379 38 49 web@lluche.com

M&U International LLC

Steady supply & demand

Meeting customers increasing demands at home as well as abroad.

View All Website 908-359-9000 sales@mu-intel.com

Penta International Corporation

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Sigma-Aldrich

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Sunaux International

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TCI AMERICA

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Tianjin Danjun International Trade Co., LTD.

Quality Products

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Ultra International Limited

Driven by a mutual passion for excellence.

Ultra International is one of the leading company in the Flavors and Fragrance industry.

View All Website 0019143161580 ultra@ultrainternational.com

Ernesto Ventós S.A.

Leaders in essence

We employ our five senses to do our job well.

View All Website +1 856 226 7501 info@ventos.com

Potential Uses

FR amber FR balsam FR clary sage oil replacer FR oriental FR woody

Natural Occurrence

clary sage oil france @ 0.10-0.20% Data clary sage oil greece @ 5.20% Data clary sage oil spain @ 0.45% Data nutmeg seed sage clary sage salvia atropatana bunge oil iran @ 13.30% Data salvia sclarea oil @ 0.06% Data thyme oil

Synonyms

alpha- ethenyl decahydro-2-hydroxy-a,2,5,5,8a-pentamethyl(1R-(1alpha(R*),2beta,4abeta,8H (1theta- (1alpha (theta),2beta, 4abeta,8aalpha))-alpha- ethenyl decahydro-2-hydroxy-alpha,2,5,5,8a-pentamethyl-1-naphthalene propanol (1r,2r,8as)-1-[(3R)-3- hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol (1R,2R,8aS)-1-[(3R)-3- hydroxy-3-methylpent-4-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol (1R-(1alpha(R*), 2beta,4abeta, 8aalpha))-2- hydroxy-alpha,2,5,5,8a-pentamethyl-alpha-vinyl decahydronaphthalene-1-propan-1-ol (13R)- labd-14-ene-8,13-diol labd-14-ene-8,13-diol, (13R)- 1- naphthalenepropanol, a-ethenyldecahydro-2-hydroxy-a,2,5,5,8a-pentamethyl-, (aR,1R,2R,4aS,8aS)- (-)- sclareol sclareol natural 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].