Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

264679

Sigma-Aldrich

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

technical grade, 80%

Synonym(s):

β-Homocyclocitral

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

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.)

functional group

aldehyde

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

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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

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)
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)
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)

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