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Merck
CN

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:
6790-58-5
Molecular Weight:
236.39
UNSPSC Code:
12352005
PubChem Substance ID:
24863228
EC Number:
229-861-2
MDL number:
MFCD00134491

Key Documents

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Product Name

(−)-Ambroxide, 99%

InChI key

YPZUZOLGGMJZJO-LQKXBSAESA-N

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

SMILES string

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

assay

99%

optical activity

[α]20/D −29°, c = 1 in toluene

mp

74-76 °C (lit.)

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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.

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.

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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Certificates of Analysis (COA)

Lot/Batch Number
MKBV3558V
MKBP3521V
MKBL6224V
MKBH2123V
MKBC3807

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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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