Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

379220

Sigma-Aldrich

(−)-Ambroxide

99%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Looking for similar products? Visit Product Comparison Guide

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service