379220
(−)-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:
Molecular Weight:
236.39
UNSPSC Code:
12352005
PubChem Substance ID:
EC Number:
229-861-2
MDL number:
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
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.
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Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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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)
Enzymes for Synthetic Biology of Ambroxide-Related Diterpenoid Fragrance Compounds
Biotechnology of Isoprenoids (2015)