We have found 46587 results matching your criteria.
Please wait while we search...
  1. 1.
    General Material Information
  2. 2.
    PhysChem Properties
  3. 3.
    Occurrences
  4. 4.
    Organoleptic Properties
  5. 5.
    Suppliers
  6. 6.
    Potential Uses
  7. 7.
    Regulatory & Documentation
  8. 8.
    Safety Information
  9. 9.
    Other Information
  10. 10.
    Blenders & Components
  11. 11.
    Literature & References

sclareol

General Material Information

Preferred name sclareol
Trivial Name (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
Formula C20 H36 O2
CAS Number 515-03-7
CAS Number 515-03-7 (RRS)
Deleted CAS Number 17904-64-2
FEMA Number 4502
Flavis Number 2.206
ECHA Number 208-194-0
FDA UNII B607NP0Q8Y
Nikkaji Number J971.072H
Beilstein Number 2054148
MDL MFCD00869558
COE Number 10311
xLogP3-AA 4.90 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 2029 (-)-sclareol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 515-03-7 ; (-)-SCLAREOL
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

US / EU / FDA / JECFA / FEMA / Scholar / Patents

Google Scholar Start search
Google Books Start search
Google Patents Start search
Perfumer & Flavorists Start search
EU Patents Start search
PubMeb Start search
NCBI Start search

Literature & References

(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
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:515-03-7
Pubchem (cid):73114
Pubchem (sid):135029099
(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
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:515-03-7
Pubchem (cid):163263
Pubchem (sid):46237757
Publications by PubMed
Characterization of two genes for the biosynthesis of abietane-type diterpenes in rosemary (Rosmarinus officinalis) glandular trichomes.
[Engineering Saccharomyces cerevisiae for sclareol production].
[Preface for special issue on synthetic biology (2013)].
Sclareol reduces CD4+ CD25+ FoxP3+ Treg cells in a breast cancer model in vivo.
Hh signaling inhibitors from Vitex negundo; naturally occurring inhibitors of the GLI1-DNA complex.
Chemical composition and anticancer activity of essential oils of Mediterranean sage (Salvia officinalis L.) grown in different environmental conditions.
Extracellular localization of the diterpene sclareol in clary sage (Salvia sclarea L., Lamiaceae).
Bioactive constituents of Salvia chrysophylla Stapf.
Toward a biosynthetic route to sclareol and amber odorants.
Enzymatic biotransformation of terpenes as bioactive agents.
A diterpene synthase from the clary sage Salvia sclarea catalyzes the cyclization of geranylgeranyl diphosphate to (8R)-hydroxy-copalyl diphosphate.
Cancer cell spheroids as a model to evaluate chemotherapy protocols.
Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture.
Identification of natural diterpenes that inhibit bacterial wilt disease in tobacco, tomato and Arabidopsis.
Sclareol exhibits anti-inflammatory activity in both lipopolysaccharide-stimulated macrophages and the λ-carrageenan-induced paw edema model.
Antimicrobial evaluation of diterpenes from Copaifera langsdorffii oleoresin against periodontal anaerobic bacteria.
First enantiospecific synthesis of marine sesquiterpene quinol akaol A.
Four potato (Solanum tuberosum) ABCG transporters and their expression in response to abiotic factors and Phytophthora infestans infection.
Synthesis of the scalarane sesterterpenoid 16-deacetoxy-12-epi-scalarafuranacetate.
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.
Isolation, chemical, and biotransformation routes of labdane-type diterpenes.
Chemical composition and antimicrobial activity of the essential oils from Cleome spinosa.
Sclareol modulates the Treg intra-tumoral infiltrated cell and inhibits tumor growth in vivo.
Mitochondria-targeted liposomes improve the apoptotic and cytotoxic action of sclareol.
Hemisynthesis of two marine cheilanthane sesterterpenes from (-)-sclareol: first enantioselective synthesis of petrosaspongiolide R.
Fragrance material review on sclareol.
Diversity of essential oil glands of clary sage (Salvia sclarea L., Lamiaceae).
Microbial hydroxylation of sclareol by Rhizopus stolonifer.
Cell growth inhibitory action of an unusual labdane diterpene, 13-epi-sclareol in breast and uterine cancers in vitro.
Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products.
Diels-Alder cycloaddition approach to puupehenone-related metabolites: synthesis of the potent angiogenesis inhibitor 8-epipuupehedione.
Liposomes modify the subcellular distribution of sclareol uptake by HCT-116 cancer cell lines.
Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice.
Structure elucidation and antibacterial activity of new fungal metabolites of sclareol.
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.
Hemisynthesis of new labdane derivatives from (-)-sclareol.
Synthesis of ent-thallusin.
A new route toward 7-Oxo-13-hydroxy-8,11,13-podocarpatrienes from labdane diterpenes.
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.
Cytotoxic and antitumor activity of liposome-incorporated sclareol against cancer cell lines and human colon cancer xenografts.
NpPDR1, a pleiotropic drug resistance-type ATP-binding cassette transporter from Nicotiana plumbaginifolia, plays a major role in plant pathogen defense.
First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol.
A comparative study of the effects of cholesterol and sclareol, a bioactive labdane type diterpene, on phospholipid bilayers.
Effect of 13-epi-sclareol on the bacterial respiratory chain.
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.
Identification of regulatory sequence elements within the transcription promoter region of NpABC1, a gene encoding a plant ABC transporter induced by diterpenes.
Antibacterial diterpenoids from Astragalus brachystachys.
The plant PDR family of ABC transporters.
Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit.
The ABC transporter SpTUR2 confers resistance to the antifungal diterpene sclareol.
Chromatographic (GC-MS, HPLC) and virological evaluations of Salvia sclarea infected by BBWV-I.
A plant plasma membrane ATP binding cassette-type transporter is involved in antifungal terpenoid secretion.
Labdane type diterpenes down-regulate the expression of c-Myc protein, but not of Bcl-2, in human leukemia T-cells undergoing apoptosis.
Biotransformation of two cytotoxic terpenes, alpha-santonin and sclareol by Botrytis cinerea.
Potential nitrite scavengers as inhibitors of the formation of N-nitrosamines in solution and tobacco matrix systems.
Synthesis of 11,12-epoxydrim-8,12-en-11-ol, 11,12-diacetoxydrimane, and warburganal from (-)-sclareol.
Synthesis and antitumoral activities of marine ent-chromazonarol and related compounds.
Chemical analysis and antimicrobial activity of the resin Ladano, of its essential oil and of the isolated compounds.
The effect of sclareol on growth and cell cycle progression of human leukemic cell lines.
A concise synthesis and in vitro cytotoxicity of new labdane diterpenes.
A concise conversion of (-)-sclareol into (+)-coronarin E and (-)-7-epi-coronarin A
[Plant anatomical and phytochemical evaluation of Salvia species].
Biorationals fromNicotiana protect cucumbers againstColletotrichum lagenarium (Pass.) ell. & halst disease development.
Terpenoids from Salvia sclarea.
Synthesis of manool-related labdane diterpenes as platelet aggregation inhibitors.
Identification of four biliary metabolites of the diterpene sclareol in the laboratory rat.
Leaf surface chemicals fromNicotiana affecting germination ofPeronospora tabacina (adam) sporangia.
Hydroxylation and glucoside conjugation in the microbial metabolism of the diterpene sclareol.
Microbial models of mammalian metabolism: fungal metabolism of the diterpene sclareol by Cunninghamella species.
Influences of diterpene sclareol glycol on some dopamine related behavior.
The effects of the diterpene sclareol glycol on seizures do not depend on central benzodiazepine receptors.
The response of diterpene sclareol glycol to acute hypoxia in mice.
[The effect of sclareol lactone and sclareol glycol on artificially induced lung metastases of Lewis lung carcinoma (a preliminary report)].
Measures of anxiety, retention and stress in the rat following treatment with the diterpene sclareol glycol.
Diterpene sclareol glycol inhibits clonidine-induced aggressive responses in mice.
Effects of the diterpene sclareol glycol on convulsive seizures.
Effects of the diterpene sclareol glycol on body temperature in rats.
[Study of the effect of sclareol glycol diterpene on the release of adenohypophysial hormones prolactin, somatotropin and adenocorticotrophic hormone].
[Study of the effect of sclareol glycol diterpene on the 3',5'-AMP level].
Experimental study of essential oils from two varieties of cultivated thyme, sesquiterpene Germacron and diterpene Sclareol for cholagogic and choleretic activity.
[Effect of diterpene sklareol glycol on the conflict test and its correlation with diazepam].
[Effects of sklareol-glycol on pentylenetetrazole-induced convulsions and its interaction with diazepam].
BIOSYNTHESIS AND METABOLISM OF (14C)SCLAREOL.
Biosynthesis of sclareol, beta-sitosterol, and oleanolic acid from mevalonic acid-2-C-14.
Biosynthesis of 14C-sclareol and beta-sitosterol from 2-14C-mevalonic acid.
[Sclareol, its chemical constitution and use in the synthesis of aromatic principles of amber; a review].
[Not Available].

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09183
HMDB (The Human Metabolome Database):HMDB36827
FooDB:FDB015776
Export Tariff Code:2906.19.5000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
FAO:(-)-Sclareol

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 308.50531005859
Melting Point 105 to 107°C @ 760 mm Hg
Boiling Point 218 to 220°C @ 19 mm Hg
Flash Point TCC Value 169.1 °C TCC
logP (o/w) 5.233 est
Solubility
alcohol Yes
water, 0.08174 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Balsamic
sweet, balsamic, sage clary sage, amber, woody, weedy
Odor strength low
Substantivity 292 hour(s) at 100.00 %
Luebke, William tgsc, (1988) At 100.00 %. sweet balsam clary amber woody weedy
Flavor Type: Woody
woody, balsamic, sage clary sage, amber, weedy, brothy, cascarilla
Luebke, William tgsc, (1988) Sweet woody balsamic clary sage amber weedy brothy cascarilla

Occurrences

Potential Uses

Applications
Odor purposes Amber, Balsam, Clary sage oil replacer, Oriental, Woody
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
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:
oral-rat LD50 > 5000 mg/kg
Food and Chemical Toxicology. Vol. 30, Pg. 115S, 1992.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Chemical Toxicology. Vol. 30, Pg. 115S, 1992.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
IFRA Critical Effect:
Dermal sensitization
IFRA Purity Specification: 98% minimum purity
IFRA fragrance material specification:
Sclareol used as a fragrance ingredient should have a minimum purity of 98%.
View the IFRA Standard
maximum skin levels for fine fragrances:
0.0200 % 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 to:
4.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics:
0.0300 %
Dermal Systemic Exposure in Cosmetic Products:
0.0008 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 Concern:1800 (μg/person/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 24
Click here to view publication 24
average usual ppmaverage maximum ppm
baked goods: 10.0000050.00000
beverages(nonalcoholic): 5.0000025.00000
beverages(alcoholic): 5.0000025.00000
breakfast cereal: 5.0000025.00000
cheese: 7.0000035.00000
chewing gum: --
condiments / relishes: 20.00000100.00000
confectionery froastings: 10.0000050.00000
egg products: --
fats / oils: 5.0000025.00000
fish products: 2.0000010.00000
frozen dairy: 7.0000035.00000
fruit ices: 10.0000050.00000
gelatins / puddings: 10.0000050.00000
granulated sugar: --
gravies: 5.0000025.00000
hard candy: 10.0000050.00000
imitation dairy: 7.0000035.00000
instant coffee / tea: 5.0000025.00000
jams / jellies: 7.0000035.00000
meat products: 2.0000010.00000
milk products: 7.0000035.00000
nut products: 5.0000025.00000
other grains: 5.0000025.00000
poultry: 2.0000010.00000
processed fruits: 7.0000035.00000
processed vegetables: 7.0000035.00000
reconstituted vegetables: 7.0000035.00000
seasonings / flavors: 5.0000025.00000
snack foods: 10.0000050.00000
soft candy: 10.0000050.00000
soups: 5.0000025.00000
sugar substitutes: --
sweet sauces: 5.0000025.00000
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 7.0000035.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 5.0000025.00000
Edible ices, including sherbet and sorbet (03.0): 10.0000050.00000
Processed fruit (04.1): 7.0000035.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 10.0000050.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 5.0000025.00000
Bakery wares (07.0): 10.0000050.00000
Meat and meat products, including poultry and game (08.0): 2.0000010.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 2.0000010.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 5.0000025.00000
Foodstuffs intended for particular nutritional uses (13.0): 10.0000050.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 5.0000025.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 10.0000050.00000
Ready-to-eat savouries (15.0): 20.00000100.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 5.0000025.00000

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 18, Revision 1 (FGE. 18 Rev1)[1] : Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical groups 6 and 8
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 90 (FGE.90): Consideration of Aliphatic, acyclic and alicyclic terpenoid tertiary alcohols and structurally related substances evaluated by JECFA (68th meeting)FGE.18Rev1 (2009)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 18, Revision 2 (FGE.18Rev2): Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical groups 6 and 8.
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 18, Revision 3 (FGE.18Rev3): Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical groups 6 and 8.
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):515-03-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :73114
National Institute of Allergy and Infectious Diseases:Data
SCCNFP:opinion
WGK Germany:2
(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
Chemidplus:0000515037
RTECS:QK0301900 for cas# 515-03-7
(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