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Merck

22135

Sigma-Aldrich

(+)-Cedrol

≥99.0% (sum of enantiomers, GC)

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C15H26O
Número de CAS:
Peso molecular:
222.37
Beilstein/REAXYS Number:
2206347
EC Number:
MDL number:
UNSPSC Code:
12352212
PubChem Substance ID:
NACRES:
NA.22

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.)

SMILES string

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

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

InChI key

SVURIXNDRWRAFU-OGMFBOKVSA-N

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General description

(+)-Cedrol is a crystalline hydrated product of α-cedrene, which is a sesquiterpene found in cedar-wood oil. 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. (±) Cedrol can be synthesized by intramolecular Diels-Alder reaction of alkyl cyclopentadiene.

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. It can also be incorporated as a precursor for the total synthesis of rare illicium sesquiterpene (+)-pseudoanisatin via selective C-H bond functionalization.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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)
Oscar Mbare et al.
BMC infectious diseases, 19(1), 800-800 (2019-09-13)
Larviciding is an effective supplementary tool for malaria vector control, but the identification and accessibility of aquatic habitats impedes application. Dissemination of the insect growth regulator, pyriproxyfen (PPF), by gravid Anopheles might constitute a novel application strategy. This study aimed
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.

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