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379220

Sigma-Aldrich

(−)-Ambroxide

99%

Synonym(s):

1,5,5,9-Tetramethyl-13-oxatricyclo[8.3.0.04,9]tridecane

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About This Item

Empirical Formula (Hill Notation):
C16H28O
CAS Number:
6790-58-5
Molecular Weight:
236.39
EC Number:
229-861-2
MDL number:
MFCD00134491
UNSPSC Code:
12352005
PubChem Substance ID:
24863228

Assay

99%

optical activity

[α]20/D −29°, c = 1 in toluene

mp

74-76 °C (lit.)

SMILES string

CC1(C)CCC[C@@]2(C)[C@H]1CC[C@@]3(C)OCC[C@H]23

InChI

1S/C16H28O/c1-14(2)8-5-9-15(3)12(14)6-10-16(4)13(15)7-11-17-16/h12-13H,5-11H2,1-4H3/t12-,13+,15-,16+/m0/s1

InChI key

YPZUZOLGGMJZJO-LQKXBSAESA-N

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General description

Ambroxide is a terpenoid, which has vast applications in the perfume industry due to its fixative property and odor. Ambergris, which was originally sourced from sperm whale, has been substituted by synthetic ambroxides.

Application

(−)-Ambroxide can be used:
  • To prepare (+)-sclareolide through C−H oxidation strategy.
  • As a substrate in C(sp3)-H alkylation/arylation studies of ethers.
  • As a substrate in the study of ethereal hydrocarbon hydroperoxidation using singlet O2.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

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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Enzymes for Synthetic Biology of Ambroxide-Related Diterpenoid Fragrance Compounds
Biotechnology of Isoprenoids (2015)
Recent developments in natural product synthesis using metal-catalysed C-H bond functionalisation
McMurray L, et al.
Chemical Society Reviews, 40(4), 1885-1898 (2011)
The Combination of Benzaldehyde and Nickel-Catalyzed Photoredox C (sp3)- H Alkylation/Arylation
Zhang L, et al.
Angewandte Chemie (International Edition in English), 58(6), 1823-1827 (2019)
Singlet oxygen-mediated selective C--H bond hydroperoxidation of ethereal hydrocarbons
Sagadevan A, et al.
Nature Communications, 8(1), 1-8 (2017)

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