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22135

Sigma-Aldrich

(+)-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
Beilstein:
2206347
EC Number:
201-035-6
MDL number:
MFCD00062952
UNSPSC Code:
12352212
PubChem Substance ID:
57647965
NACRES:
NA.22

Quality Level

100

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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
Catalytic acetylation of (+)-cedrol with heterogeneous catalyst H2SO4/SiO2 under solvent free conditions
Elvia R, et al.
Chemical Intermediates, 1(4), 196-201 (2015)
Bushra Abdulkarim Moharam et al.
Molecules (Basel, Switzerland), 15(8), 5124-5138 (2010-08-18)
Nine essential oils, hydrodistilled from different parts of five Goniothalamus species (G. velutinus Airy-Shaw, G. woodii Merr., G. clemensii Ban, G. tapis Miq. and G. tapisoides Mat Salleh) were evaluated for their ability to inhibit platelet aggregation in human whole
Anthony J Pearson et al.
Organic letters, 6(15), 2535-2538 (2004-07-17)
[reaction: see text] A short and convenient diastereoselective synthesis of all-carbon spirocylic molecules was developed. A straightforward protocol that involves rearrangement of the diene-Fe(CO)(3) complex followed by cyclization delivers the desired product. The reaction substrates were easily prepared by reaction
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