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357995

Sigma-Aldrich

Sclareol

98%

Synonym(s):

Labd-14-ene-8,13-diol, (1R,2R,8aS)-Decahydro-1-(3-hydroxy-3-methyl-4-pentenyl)-2,5,5,8a-tetramethyl-2-naphthol

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About This Item

Empirical Formula (Hill Notation):
C20H36O2
CAS Number:
515-03-7
Molecular Weight:
308.50
Beilstein:
2054148
EC Number:
208-194-0
MDL number:
MFCD00869558
UNSPSC Code:
12352002
PubChem Substance ID:
24861955
NACRES:
NA.22

Assay

98%

optical activity

[α]25/D −13°, c = 4 in carbon tetrachloride

bp

218-220 °C/19 mmHg (lit.)

mp

95-100 °C (lit.)

functional group

hydroxyl

SMILES string

CC1(C)CCC[C@@]2(C)[C@H]1CC[C@@](C)(O)[C@@H]2CC[C@@](C)(O)C=C

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

InChI key

XVULBTBTFGYVRC-HHUCQEJWSA-N

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General description

Sclareol, a diterpene compound with a labdane skeleton, is mainly used as a raw material in the fragrance industry. It shows potent cytotoxic and cytostatic effect in human leukemic cell lines.

Application

Sclareol may be used as a starting material in the synthesis of ambergris fragrance chemicals such as ambraoxide, ambrox, methylambraoxide, ambracetal, ambraketal and epiambraketal. It may also be used in the synthesis of (+)-galanolactone, (-)-8-epi-galanolactone and (+)-labdienedial.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

357995-1G:
357995-VAR:
357995-100G:
357995-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
STBG9905
STBD5592V
S44114V
S44114
S39525

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The effect of sclareol on growth and cell cycle progression of human leukemic cell lines.
Dimas K, et al.
Leukemia Research, 23(3), 217-234 (1999)
Synthesis of ambergris fragrance chemicals from sclareol, involving palladium catalysed key steps.
Coste-Maniere IC, et al.
Tetrahedron Letters, 29(9), 1017-1020 (1988)
Conversion of sclareol into (+)-galanolactone and (+)-labdienedial.
Jung M, et al.
Tetrahedron Letters, 38(16), 2871-2874 (1997)
Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture.
Caniard A, et al.
BMC plant biology, 12(1), 119-119 (2012)
A short efficient synthesis of ambraketal (four steps) and epiambraketal (five steps) from Sclareol.
Martres P, et al.
Tetrahedron Letters, 35(1), 97-98 (1994)
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