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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

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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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)
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)
Enzymes for Synthetic Biology of Ambroxide-Related Diterpenoid Fragrance Compounds
Biotechnology of Isoprenoids (2015)
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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