2,6-Dimethyl-5-heptenal

2,6-Dimethyl-5-heptenal Basic information
Product Name:2,6-Dimethyl-5-heptenal
Synonyms:,6-Dimethyl hept-5-en-1-al;2,6-dimethyl-5-heptena;2,6-dimethylhept-;2,6-dimethylhept-5-en-1-al;ai3-33278;nsc78450;Dimethylheptenal;2,6-Dimethyl-2-hepten-7-al
CAS:106-72-9
MF:C9H16O
MW:140.22
EINECS:203-427-2
Product Categories:
Mol File:106-72-9.mol
2,6-Dimethyl-5-heptenal Structure
2,6-Dimethyl-5-heptenal Chemical Properties
Boiling point 116-124 °C100 mm Hg(lit.)
density 0.879 g/mL at 25 °C
vapor pressure 2.39hPa at 25℃
FEMA 2389 | 2,6-DIMETHYL-5-HEPTENAL
refractive index n20/D 1.444(lit.)
Fp 141 °F
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
form Liquid
Specific Gravity0.879
color Light orange to Yellow to Green
Odorat 1.00 % in dipropylene glycol. fresh ozone melon fresh air sweet clean green
Odor Typemelon
Water Solubility Soluble in alcohol, paraffin oil. Insoluble in water.
Sensitive Air Sensitive
JECFA Number349
InChIKeyYGFGZTXGYTUXBA-UHFFFAOYSA-N
LogP3.4
CAS DataBase Reference106-72-9(CAS DataBase Reference)
NIST Chemistry Reference5-Heptenal, 2,6-dimethyl-(106-72-9)
EPA Substance Registry System5-Heptenal, 2,6-dimethyl- (106-72-9)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36/37/39
RIDADR 1987
WGK Germany 2
RTECS MJ8797000
Hazard Note Irritant
TSCA Yes
HazardClass 3
PackingGroup III
HS Code 29121900
toxicityBoth the acute oral LD50 value in rats and the acute dermal LD50 value in rabbits exceeded 5 g/kg (Levenstein, 1974).
MSDS Information
ProviderLanguage
2,6-Dimethyl-2-hepten-7-alEnglish
SigmaAldrichEnglish
ALFAEnglish
2,6-Dimethyl-5-heptenal Usage And Synthesis
Chemical Properties2,6-Dimethyl-5-hepten-1-al was identified in ginger. It is a yellow liquid with a powerful, green, cucumber-like, and melon odor. It can be prepared by Darzens reaction of 6-methyl-5-hepten-2-one with ethyl chloroacetate. The intermediate glycidate is saponified and decarboxylated to yield the title compound.
It is used in many fragrance types and is invaluable in the creation ofmelon and cucumber notes.
Chemical Properties2,6-Dimethyl-5-heptenal has a characteristic odor of melon and a corresponding taste.
OccurrenceReported found in lemon and lime peel oil, sudachi (Citrus sudachi H. ex. Shirai) and ginger.
UsesIt is used or fragrances designed to have a special fruity note tending towards melon, cucumber and pumpkin. It is mainly used perfuming agents.
PreparationBy condensation of isobutyric aldehyde with α-methylcrotonaldehyde, followed by par tial hydrogenation; also from methylheptenone through Darzen’s reaction.
Aroma threshold valuesDetection: 16 ppb
Taste threshold valuesTaste characteristics at 50 ppm: green, melon, watermelon-rind, cucumber, with a waxy, chemical and floral nuance.
General Description2,6-Dimethyl-5-heptenal (melonal) and 5-heptenal undergo concerted ene reaction to form zwitterion that further reacts to give ene product.
Flammability and ExplosibilityNotclassified
Trade nameMelonal (Givaudan), Melomor (Aromor).
Safety Profileskin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
2,6-Dimethyl-5-heptenal Preparation Products And Raw materials
Raw materialsIsobutyraldehyde–>Crotonaldehyde
Preparation ProductsMETHOPRENE

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