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sclareolide

Chemical Structure

General Material Information

Preferred name sclareolide
Trivial Name (+)-Sclareolide
Short Description (R)-(+)-sclareolide
Formula C16 H26 O2
CAS Number 564-20-5
FEMA Number 3794
Flavis Number 16.055
ECHA Number 209-269-0
FDA UNII 37W4O0O6E6
Nikkaji Number J217.066C
MDL MFCD00134168
COE Number 16055
xLogP3-AA 4.30 (est)
NMR Predictor External link
JECFA Food Flavoring 1165 sclareolide
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 564-20-5 ; SCLAREOLIDE
Synonyms
  • (+)-nor ambreinolide
  • 12-nor ambrienolide
  • (3ar- (3aalpha,5abeta, 9aalpha,9bbeta)) decahydro-3a,6,6,9a-tetramethyl naphth(2,1-b)furan-2(1H)-one
  • (3aR,5aS,9aS,9bR)- decahydro-3a,6,6,9a-tetramethyl naphtho(2,1-b)furan-2(1H)-one
  • decahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b)furan-2(1H)-one
  • decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one
  • 3a,4,5,5aalpha, 6,7,8,9,9a,9balpha- decahydro-3abeta,6,6,9abeta-tetramethyl naphtho(2,1-b)furan-2(1H)-one
  • 3a,4,5,5aa,6,7,8,9,9a,9ba- decahydro-3aβ,6,6,9aβ-tetramethylnaphtho(2,1-b)furan-2(1H)-one
  • naphtho 2,1-b furan-2(1H)-one, decahydro-3a,6,6,9a-tetramethyl-,
  • naphtho(2,1-b)furan-2(1H)-one, decahydro-3a,6,6,9a-tetramethyl-
  • naphtho[2,1-b]furan-2(1H)-one, decahydro-3a,6,6,9a-tetramethyl-
  • (3aR)-(+)- sclareolide
  • (R)-(+)- sclareolide
  • sclareolide natural
  • slareolide natural
  • (3aR,5aS,9aS,9bR)-3a,6,6,9a- tetramethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[e][1]benzofuran-2-one
  • 3a,6,6,9a- tetramethyl-1,4,5,5a,7,8,9,9b-octahydronaphtho[8,7-d]furan-2-one
  • 3a,6,6,9a- tetramethyl-decahydro-naphtho[2,1-b]furan-2-one
  • 3a,6,6,9a- tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-one
  • Naphtho[2,1-b]furan-2(1H)-one, decahydro-3a,6,6,9a-tetramethyl-, (3aR,5aS,9aS,9bR)-
  • Norambreinolide
  • Naphtho[2,1-b]furan-2(1H)-one, 3a,4,5,5aα,6,7,8,9,9a,9bα-decahydro-3aβ,6,6,9aβ-tetramethyl-
  • Naphtho[2,1-b]furan-2(1H)-one, decahydro-3a,6,6,9a-tetramethyl-, [3aR-(3aα,5aβ,9aα,9bβ)]-
  • (3aR,5aS,9aS,9bR)-Decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one
  • (+)-Norambreinolide
  • Norambreinolid
  • (+)-Sclareolide
  • (R)-(+)-Sclareolide
  • 13,14,15,16-Tetranorlabdano-8α,12-lactone
  • (3αR)-(+)-Sclareolide
  • (3aR)-(+)-Sclareolide
  • (3AR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-one

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

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Literature & References

(3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[e][1]benzofuran-2-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:564-20-5
Pubchem (cid):61129
Pubchem (sid):135017861
Publications by PubMed
Synthesis of Labdane Diterpenes Galanal A and B from (+)-Sclareolide.
Analysis of gene profiles involved in the enhancement of all-trans retinoic acid-induced HL-60 cell differentiation by sesquiterpene lactones identifies asparagine synthetase as a novel target for differentiation-inducing therapy.
Enhanced reactivity in dioxirane C-H oxidations via strain release: a computational and experimental study.
Total synthesis of (+)-aureol.
Scalable, divergent synthesis of meroterpenoids via "borono-sclareolide".
Isolation, chemical, and biotransformation routes of labdane-type diterpenes.
Exploiting the facile release of trifluoroacetate for the α-methylenation of the sterically hindered carbonyl groups on (+)-sclareolide and (-)-eburnamonine.
Manganese porphyrins catalyze selective C-H bond halogenations.
Synthesis and biological evaluation of (+)-labdadienedial, derivatives and precursors from (+)-sclareolide.
Enantiospecific, biosynthetically inspired formal total synthesis of (+)-liphagal.
Differential enhancement of leukaemia cell differentiation without elevation of intracellular calcium by plant-derived sesquiterpene lactone compounds.
Structure revision and synthesis of a novel labdane diterpenoid from Zingiber ottensii.
Synthesis of (+)-zerumin B using a regioselective singlet oxygen furan oxidation.
(3aS,7S,9aS,9bR)-3a,6,6,9a-Tetra-methyl-2-oxoperhydro-naphtho[2,1-b]furan-7-yl acetate.
Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products.
Novel microbial transformations of sclareolide.
Chiral decalins: preparation from oleanolic acid and application in the synthesis of (-)-9-epi-ambrox.
Synthesis and stereochemistry of the antitumor diterpenoid (+)-zerumin B.
The nicholas approach to natural product hybrids.
Synthesis of alpha-onoceradiene-like terpene dimers by intermolecular metathesis processes.
Synthesis and biological activity of (+)-hedychilactone A and its analogs from (+)-sclareolide.
Diversity oriented synthesis of hispanane-like terpene derivatives from (R)-(+)-sclareolide.
Synthesis of pelorol and analogues: activators of the inositol 5-phosphatase SHIP.
Photochemical access to tetra- and pentacyclic terpene-like products from R-(+)-sclareolide.
Identification of regulatory sequence elements within the transcription promoter region of NpABC1, a gene encoding a plant ABC transporter induced by diterpenes.
A study on the synthesis of antiangiogenic (+)-coronarin A and congeners from (+)-sclareolide.
Enantiospecific synthesis of the antituberculosis marine sponge metabolite (+)-puupehenone. The arenol oxidative activation route.
The ABC transporter SpTUR2 confers resistance to the antifungal diterpene sclareol.
An approach to furolabdanes and their photooxidation derivatives from R-(+)-sclareolide.
Total synthesis and determination of the absolute configuration of coscinosulfate. A new selective inhibitor of Cdc25 protein phosphatase.
A plant plasma membrane ATP binding cassette-type transporter is involved in antifungal terpenoid secretion.
Oxidative metabolism of ambrox and sclareolide by Botrytis cinerea.
Microbial transformation of sclareolide.

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
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB35293
FooDB:FDB013958
Export Tariff Code:2932.99.9090
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 250.38162231445
Melting Point 124 to 127°C @ 760 mm Hg
Boiling Point 320 to 321°C @ 760 mm Hg
Vapor Pressure 0.000299 mmHg @ 25 °C
Flash Point TCC Value 132.22 °C TCC
logP (o/w) 4.151 est
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
diethyl phthalate Yes
isopropyl myristate Yes
water, 11.99 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Woody
dry, paper, woody, ambergris, labdanum, aromatic, mossy, cedar, tobacco
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 108 hour(s) at 10.00 % in dipropylene glycol
Luebke, William tgsc, (2007) At 10.00 % in isopropyl myristate. dry paper woody ambergris labdanum
Mosciano, Gerard P&F 26, No. 3, 80, (2001) At 1.00 %. Intense, aromatic, woody and moss like with a cedar and tobacco nuance
Flavor Type: Woody
aromatic, woody, cedar, tobacco, mushroom, earthy, oakmoss
Mosciano, Gerard P&F 26, No. 3, 80, (2001) At 0.10 - 5.00 ppm. Intense aromatic, woody, cedar like, tobacco with a mushroom and earthy nuance. It has a vague perfumey oak moss note

Occurrences

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.
S 36 - Wear suitable protective clothing.
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:
cosmetic, 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
Recommendation for sclareolide usage levels up to:
0.5000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 1.10 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 6.00 (μg/capita/day)
Structure Class: III
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: 16
Click here to view publication 16
average usual ppmaverage maximum ppm
baked goods: 2.000003.00000
beverages(nonalcoholic): 1.000005.00000
beverages(alcoholic): 1.000005.00000
breakfast cereal: 1.000003.00000
cheese: 1.000003.00000
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: 1.000002.00000
fish products: 1.000002.00000
frozen dairy: 1.000003.00000
fruit ices: --
gelatins / puddings: 1.000002.00000
granulated sugar: --
gravies: 1.000002.00000
hard candy: 1.000003.00000
imitation dairy: 3.0000010.00000
instant coffee / tea: --
jams / jellies: --
meat products: 1.000004.00000
milk products: 2.000004.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: 1.000002.00000
reconstituted vegetables: 1.000002.00000
seasonings / flavors: 1.000003.00000
snack foods: 2.000004.00000
soft candy: 1.000003.00000
soups: 1.000002.00000
sugar substitutes: 1.000003.00000
sweet sauces: 1.000002.00000

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 80 (FGE.80) - Consideration of alicyclic, alicyclic-fused and aromatic-fused ring lactones evaluated by JECFA (61st meeting) structurally related to a aromatic lactone evaluated by EFSA in FGE.27 (2008)
View page or View pdf

Flavouring Group Evaluation 80, Revision 1 (FGE.80Rev1): Consideration of alicyclic, alicyclic-fused and aromatic-fused ring lactones evaluated by JECFA (61st meeting) structurally related to a aromatic lactone evaluated by EFSA in FGE.27 (2008)
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):564-20-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :61129
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
(3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[e][1]benzofuran-2-one
Chemidplus:0000564205