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[1R-[1α(R*),2β,4aβ,8aα]]-2-Hydroxy-α,2,5,5,8a-pentamethyl-α-vinyldecahydronaphthalin-1-propan-1-ol

Sclareol

HCID 163263
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Grundinformationen

CAS
515-03-7
Standard-SMILES
C=C[C@](C)(O)CC[C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2CC[C@@]1(C)O
InChIKey
XVULBTBTFGYVRC-HHUCQEJWSA-N
Summenformel
C20H36O2
Durchschnittliche Molmasse
308,5 g/mol
Monoisotopische Masse
308,27153039

Namen und Bezeichner

Bevorzugter Name
Sclareol
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
Lokaler Name
[1R-[1α(R*),2β,4aβ,8aα]]-2-Hydroxy-α,2,5,5,8a-pentamethyl-α-vinyldecahydronaphthalin-1-propan-1-ol
Englischer Name
Sclareol
Summenformel
C20H36O2
Molmasse
308.51

Namen und Synonyme

Sclareol515-03-7labd-14-ene-8,13-diolDTXSID0047111(13R)-Labd-14-ene-8,13-diol(-)-SCLAREOLB607NP0Q8YLabd-14-ene-8,13-diol, (13R)-CHEBI:9053DTXCID8027111FEMA NO. 4502(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
Weitere Namen anzeigen
SCIADONIC ACIDNatural sclareol1-Naphthalenepropanol, α-ethenyldecahydro-2-hydroxy-α,2,5,5,8a-pentamethyl-, (αR,1R,2R,4aS,8aS)-SCAREOLAids046592SCLAREOL(P)Aids-046592SCLAREOL(RG)
1-Naphthalenepropanol, alpha-ethenyldecahydro-2-hydroxy-alpha,2,5,5,8a-pentamethyl-, (alphaR,1R,2R,4aS,8aS)-labd-14-ene-8alpha, 13beta-diol(1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol labd-14-ene-8,13-diol(1R,2R,4aS,8aS)-1-((3R)-3-hydroxy-3-methylpent-4-en-1-yl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol labd-14-ene-8,13-diol(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-olRefChem:49009208-194-0(1R,2R,4aS,8aS)-1-((R)-3-hydroxy-3-methylpent-4-en-1-yl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,9
Polarare Oberfläche (TPSA)
40,5 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
4
Schwere Atome
22
Formalladung
0
Komplexität
429

Experimentelle und physikochemische Eigenschaften

Solubility · 2 Einträge

Practically insoluble or insoluble in water

Soluble (in ethanol)

Physical Description · 2 Einträge

Large Crystals

Solid; Bitter herbaceous hay-like aroma

Collision Cross Section189.2 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0047111];178.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID0047111]

Physikochemische Eigenschaften

Schmelzpunkt
95 · 95-100 °C (lit.)
Siedepunkt
218 · 218-220 °C/19 mmHg (lit.)
Dichte
0.954 · 0.954±0.06 g/cm3(Predicted)
FEMA
4502 · 4502 | (-)-SCLAREOL
storage temp.
2 · 2-8°C
Löslichkeit
Chlorform, Ethyl Acetate (Slightly)
pka
14.49 · 14.49±0.29(Predicted)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 3 Einträge

This chemical does not meet GHS hazard criteria for 99.2% (131 of 132) of all reports.

Not Classified;Reported as not meeting GHS hazard criteria by 131 of 132 companies (only 0.8% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

Aggregated GHS information provided per 132 reports by companies from 3 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 131 of 132 reports by companies.;There is 1 notification provided by 1 of 132 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: 1-Naphthalenepropanol, .alpha.-ethenyldecahydro-2-hydroxy-.alpha.,2,5,5,8a-pentamethyl-, [1R-[1.alpha.(R*),2.beta.,4a.beta.,8a.alpha.]]-

Hazard Traits - Bioaccumulation; Environmental Persistence; Fragrance Allergen;Authoritative List - Annex III of the EU Cosmetics Regulation No. 1223/2009 - Fragrance Allergens; Canada PBiTs;Report - if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million);Report - if used as a fragrance or flavor ingredient

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

1-Naphthalenepropanol, .alpha.-ethenyldecahydro-2-hydroxy-.alpha.,2,5,5,8a-pentamethyl-, (.alpha.R,1R,2R,4aS,8aS)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Naphthalenepropanol, .alpha.-ethenyldecahydro-2-hydroxy-.alpha.,2,5,5,8a-pentamethyl-, (.alpha.R,1R,2R,4aS,8aS)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Chemie und Industrie

Verwendung und Herstellung

U.S. Production2023: 293,265 lb;2022: 550,000 - <1,000,000 lb;2021: 250,000 - <550,000 lb;2020: 250,000 - <550,000 lb
Consumer UsesIntermediate
Industry UsesIntermediate
IFRA Fragrance Standards · 6 Einträge

Sclareol

Labd-14-ene-8,13-diol; 1-Naphthalenepropanol,decahydro-alpha-ethenyl-2-hydroxy- alpha,2,5,5,8apentamethyl-, (1R-(1-alpha(R*),2-beta,4a-beta,8a-alpha))-

IFRA_STD_183.pdf

39

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Specification: This material should be used only if it meets the criteria stated in the Standard

Household Products · 1 Eintrag

Cosmetics product ingredient: 1-Naphthalenepropanol, a-ethenyldecahydro- 2-hydroxy-a,2,5,5,8a-pentamethyl-, [1R-[1a(R),2ß,4aß,8aa]]- (Sclareol; [1R-(1alpha)]-alpha-Ethenyldecahydro-2-hydroxy-a,2,5,5,8a-pentamethyl-1-naphthalenepropanol);Sclareol is a fragrance allergen. Fragrance allergens are hazardous only to individuals who suffer from fragrance allergies. The Cosmetic Fragrance and Flavor Ingredient Right to Know Act of 2020 requires fragrance allergens included in Annex III of the EU Cosmetics Regulation No. 1223/2009 be reported to the California Department of Public Health. Fragrance allergens are only required to be reported if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million).;Reason for Listing: Listed as Persistent, Bioaccumulative, and Inherently Toxic to the environment by the Canadian Environmental Protection Act Environmental Registry Domestic Substances List.;Potential Health Impacts: Bioaccumulation, Environmental Persistence, and Undefined Toxicity;For more information, you can visit the fragrance allergens webpage on the California Safe Cosmetics Program website:;https://www.cdph.ca.gov/Programs/CCDPHP/DEODC/OHB/CSCP/Pages/FragranceAllergens.aspx;Product count: 227

Use Classification · 3 Einträge

Zugehörige Reaktionen

7
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 399619
HRID 399619als Eduktuspto-grants-1998_10
Reaktionsgleichung von HRID 659928
HRID 659928als Produktuspto-grants-2011_12
Reaktionsgleichung von HRID 659929
HRID 659929als Eduktuspto-grants-2011_12
Reaktionsgleichung von HRID 844589
HRID 844589als Eduktuspto-grants-2002_04
Reaktionsgleichung von HRID 2066362
HRID 2066362als Produktuspto-grants-2012_10
Reaktionsgleichung von HRID 2066363
HRID 2066363als Eduktuspto-grants-2012_10
Reaktionsgleichung von HRID 2291811
HRID 2291811als Eduktuspto-grants-1989_01

Notizen zur Verbindung

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Datenbank-Bezeichner

CAS
515-03-7
PubChem CID
163263
DTXSID
DTXSID0047111
ChEMBL
CHEMBL294740
ChEBI
CHEBI:9053
UNII
B607NP0Q8Y
EC Number
208-194-0
Nikkaji
J13.989K
Aggregatzustand
Solid
Farbe
White to Off-White
Geruch (Odor)
100 % · at 100.00 %. sweet balsam clary amber woody weedy
Geruchsart
balsamic
Biologische Quelle
Salvia sclarea L
JECFA Number
2029 · 2029
BRN
2054148 · 2054148
Major Application
cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care
Kosmetik-Inhaltsstoffe Funktionen
PERFUMING
InChI
1S/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1
InChIKey
XVULBTBTFGYVRC-HHUCQEJWSA-N
SMILES
CC1(C)CCC[C@@]2(C)[C@H]1CC[C@@](C)(O)[C@@H]2CC[C@@](C)(O)C=C
LogP
5.54 · 5.54
CAS Datenbank
515 · 515-03-7(CAS DataBase Reference)
NIST chemische Informationen
1 · 1-Naphthalenepropanol, «alpha»-ethenyldecahydro-2-hydroxy-«alpha»,2,5,5,8a-pentamethyl-, [1r-[1«alpha»(r*),2«beta»,4a«beta»,8a«alpha»]]-(515-03-7)
EPA chemische Informationen
Sclareol (515-03-7)

Status: Active Update: 04-09-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/21269

1-Naphthalenepropanol, .alpha.-ethenyldecahydro-2-hydroxy-.alpha.,2,5,5,8a-pentamethyl-, (.alpha.R,1R,2R,4aS,8aS)-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 1-Naphthalenepropanol, .alpha.-ethenyldecahydro-2-hydroxy-.alpha.,2,5,5,8a-pentamethyl-, [1R-[1.alpha.(R*),2.beta.,4a.beta.,8a.alpha.]]-: Human health tier I assessment
Hazard Classes and CategoriesNot Classified

Regulatorische Informationen

Regulatory Information · 6 Einträge

Chemical: 1-Naphthalenepropanol, .alpha.-ethenyldecahydro-2-hydroxy-.alpha.,2,5,5,8a-pentamethyl-, [1R-[1.alpha.(R*),2.beta.,4a.beta.,8a.alpha.]]-

Hazard Traits - Bioaccumulation; Environmental Persistence; Fragrance Allergen;Authoritative List - Annex III of the EU Cosmetics Regulation No. 1223/2009 - Fragrance Allergens; Canada PBiTs;Report - if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million);Report - if used as a fragrance or flavor ingredient

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

1-Naphthalenepropanol, .alpha.-ethenyldecahydro-2-hydroxy-.alpha.,2,5,5,8a-pentamethyl-, (.alpha.R,1R,2R,4aS,8aS)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Naphthalenepropanol, .alpha.-ethenyldecahydro-2-hydroxy-.alpha.,2,5,5,8a-pentamethyl-, (.alpha.R,1R,2R,4aS,8aS)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 04-09-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/21269

1-Naphthalenepropanol, .alpha.-ethenyldecahydro-2-hydroxy-.alpha.,2,5,5,8a-pentamethyl-, (.alpha.R,1R,2R,4aS,8aS)-: Does not have an individual approval but may be used under an appropriate group standard

Sicherheitsdaten

wgk
2
tsca
TSCA listed
hs_code
29061990
RTECS-Nr.
QK0301900
Speicherklasse
11 - Combustible Solids

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information · 2 Einträge

All Other Basic Organic Chemical Manufacturing

1-Naphthalenepropanol, .alpha.-ethenyldecahydro-2-hydroxy-.alpha.,2,5,5,8a-pentamethyl-, (.alpha.R,1R,2R,4aS,8aS)-: ACTIVE

Anwendungen

VerwendenSclareol is used in biological studies as it has anti-inflammatory activity in both lipopolysaccharide-stimulated macophages and λ-carrageenan-induced paw edema model.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

MANOOL1-Naphthalenepropanol,2-(acetyloxy)-a-ethenyldecahydro-a,2,5,5,8a-pentamethyl-,acetate,(aR,1R,2R,4aS,8aS)- (9CI)Clary sage oil

Nachgelagerte Produkte

Bicyclohomofarnesal[3aR-(3aα,5aβ,9aα,9bβ)]-Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan

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Ergänzende Hinweise

DefinitionChEBI: A labdane diterpenoid that is labd-14-ene substituted by hydroxy groups at positions 8 and 13. It has been isolated from Salvia sclarea.