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264679

Sigma-Aldrich

2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde

technical grade, 80%

Synonym(s):

β-Homocyclocitral

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About This Item

Empirical Formula (Hill Notation):
C11H18O
CAS Number:
472-66-2
Molecular Weight:
166.26
EC Number:
207-454-0
MDL number:
MFCD00012057
UNSPSC Code:
12352100
PubChem Substance ID:
24856029
NACRES:
NA.22

grade

technical grade

assay

80%

form

liquid

refractive index

n20/D 1.485 (lit.)

bp

58-59 °C/0.4 mmHg (lit.)

density

0.941 g/mL at 25 °C (lit.)

SMILES string

[H]C(=O)CC1=C(C)CCCC1(C)C

InChI

1S/C11H18O/c1-9-5-4-7-11(2,3)10(9)6-8-12/h8H,4-7H2,1-3H3

InChI key

VHTFHZGAMYUZEP-UHFFFAOYSA-N

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Application

2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde can be used as a starting material to prepare:
  • (±)-Aeginetolide by oxidation in the presence of meta-chloroperoxybenzoic acid (m-CPBA).
  • (±)-Dihydroactinidiolide (a C11-terpenic lactone) via dehydration of key intermediate aeginetolide.

It can also be used as a key intermediate to synthesize drimane-related sesquiterpenes and substituted retinoic acid analogs.

Other Notes

Contains β-cyclocitral

Pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Preparation and biological activity of 13-substituted retinoic acids
Wada A, et al.
Bioorganic & Medicinal Chemistry, 12(14), 3931-3942 (2004)
An improved synthesis of (?)-dihydroactinidiolide
Subbaraju GV, et al.
Tetrahedron Letters, 32(37), 4871-4874 (1991)
Improved Synthesis of 2, 6, 6-Trimethyl-1-cyclohexene-1-acetaldehyde, A Key Intermediate for Drimane-Related Sesquiterpenes
de Jong JC, et al.
Synthetic Communications, 20(4), 589-596 (1990)
An improved synthesis of (?)-dihydroactinidiolide.
Subbaraju GV, et al.
Tetrahedron Letters, 32(37), 4871-4874 (1991)
Improved Synthesis of 2, 6, 6-Trimethyl-1-cyclohexene-1-acetaldehyde, A Key Intermediate for Drimane-Related Sesquiterpenes.
de Jong JC, et al.
Synthetic Communications, 20(4), 589-596 (1990)

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