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About This Item
Empirical Formula (Hill Notation):
C16H28O
CAS Number:
Molecular Weight:
236.39
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
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
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)
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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