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22135

(+)-Cedrol

≥99.0% (sum of enantiomers, GC)

Synonym(s):

(1S,2R,5S,7R,8R)-2,6,6,8-Tetramethyltricyclo[5.3.1.01.5]undecan-8-ol

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About This Item

Empirical Formula (Hill Notation):
C15H26O
CAS Number:
77-53-2
Molecular Weight:
222.37
UNSPSC Code:
12352212
NACRES:
NA.22
PubChem Substance ID:
57647965
EC Number:
201-035-6
Beilstein/REAXYS Number:
2206347
MDL number:
MFCD00062952

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Product Name

(+)-Cedrol, ≥99.0% (sum of enantiomers, GC)

InChI key

SVURIXNDRWRAFU-OGMFBOKVSA-N

InChI

1S/C15H26O/c1-10-5-6-11-13(2,3)12-9-15(10,11)8-7-14(12,4)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14-,15+/m1/s1

SMILES string

C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CC[C@@]3(C)O

assay

≥99.0% (sum of enantiomers, GC)

form

solid

optical activity

[α]20/D +10.5±1°, c = 5% in chloroform

bp

273 °C (lit.)

mp

82-86 °C
86-87 °C (lit.)

functional group

hydroxyl

Quality Level

100

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This Item
221342213358924
(+)-Cedrol ≥99.0% (sum of enantiomers, GC)

Sigma-Aldrich

22135

(+)-Cedrol

(+)-β-Cedrene ≥95.0% (sum of enantiomers, GC)

Sigma-Aldrich

22134

(+)-β-Cedrene

(−)-α-Cedrene ≥95.0% (sum of enantiomers, GC)

Sigma-Aldrich

22133

(−)-α-Cedrene

(−)-Isolongifolene ≥98.0% (sum of enantiomers, GC)

Sigma-Aldrich

58924

(−)-Isolongifolene

assay

≥99.0% (sum of enantiomers, GC)

assay

≥95.0% (sum of enantiomers, GC)

assay

≥95.0% (sum of enantiomers, GC)

assay

≥98.0% (sum of enantiomers, GC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

bp

273 °C (lit.)

bp

263-264 °C (lit.)

bp

261-262 °C (lit.)

bp

255-256 °C

form

solid

form

liquid

form

liquid

form

-

mp

82-86 °C

mp

-

mp

-

mp

-

optical activity

[α]20/D +10.5±1°, c = 5% in chloroform

optical activity

[α]/D 11.5 to 14.5°, c = 1 in chloroform

optical activity

[α]20/D −88±1°, c = 10% in ethanol

optical activity

[α]20/D −138±2°, c = 1% in ethanol

Application

(+)-Cedrol can be used as a starting material for the preparation of cedryl acetate by acetylation using acetic anhydride in the presence of an acid catalyst.[1] It can also be incorporated as a precursor for the total synthesis of rare illicium sesquiterpene (+)-pseudoanisatin via selective C-H bond functionalization.[2]

General description

(+)-Cedrol is a crystalline hydrated product of α-cedrene, which is a sesquiterpene found in cedar-wood oil.[3] It can be used as a fragrance ingredient in cosmetics, shampoos, and soaps as well as in non-cosmetic products such as cleaners and detergents.[1] (±) Cedrol can be synthesized by intramolecular Diels-Alder reaction of alkyl cyclopentadiene.[3]

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN9278
BCCL9557
BCCK2342
BCCG1845
BCCF3081

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Catalytic acetylation of (+)-cedrol with heterogeneous catalyst H2SO4/SiO2 under solvent free conditions
Elvia R, et al.
Chemical Intermediates, 1(4), 196-201 (2015)
Kevin Hung et al.
Journal of the American Chemical Society, 138(51), 16616-16619 (2016-12-15)
Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50
Total synthesis of (.+-.)-cedrol and (.+-.)-cedrene via an intramolecular Diels-Alder reaction
Breitholle EG and Fallis AG
The Journal of Organic Chemistry, 43(10), 1964-1968 (1978)
Mitsuo Miyazawa et al.
Natural product research, 17(5), 313-317 (2003-10-07)
Microbial transformation of (+)-cedrol was investigated by using Staphylococcus epidermidis and found that stereospecific hydroxylation of (+)-cedrol occurred at the C-3 position to form (+)-(3S)-3-hydroxycedrol.
L Hua et al.
Archives of biochemistry and biophysics, 369(2), 208-212 (1999-09-16)
A cDNA library was prepared from Artemisia annua, and a 129-bp fragment was amplified from this library using primers corresponding to sequences conserved in known dicot sesquiterpene synthases. A 1641-bp open reading frame that encoded a predicted protein 35-38% identical
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