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357995

Sclareol

Name: Sclareol
Brand: ALDRICH

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

UNSPSC Code:

12352002

NACRES:

NA.22

PubChem Substance ID:

24861955

EC Number:

208-194-0

Beilstein/REAXYS Number:

2054148

MDL number:

MFCD00869558

Assay:

98%

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Properties

Quality Level

100

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

Description

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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)

Conversion of sclareol into (+)-galanolactone and (+)-labdienedial.

Jung M, et al.

Tetrahedron Letters, 38(16), 2871-2874 (1997)

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Global Trade Item Number

SKU	GTIN
357995-1G	04061831812749