Description
2-Hexen-l-ol has a powerful, fruity, green, wine-like, leafy odor
and a sweet, fruity flavor important to strawberry and orange juice.
The ds-form can be prepared by hydrogenation of ds-2-hexenol,
using an aqueous suspension of colloidal palladium; from cis-
4-chloro-2-butenol and magnesium ethyl bromide; the commercial
product is a mixture of the cis- and trans-isomers and can be
prepared from propyl vinyl carbinol by heating with aluminum
oxide.
Chemical Properties
2-Hexen-1-ol has a powerful, fruity-green odor, with a sweet, fruity flavor important to strawberry and orange juice
Occurrence
Reported found as a constituent of fresh raspberry aroma; also identified in Valencia orange juice and apple
aroma, probably occurring as an ester. Also reported found in raw and cooked asparagus, cooked potato, cooked beef, hop oil,
brandy, beer, white wine, roasted peanut, soybean, olive, prune, prickly pear, malt, kiwifruit, loquat, quince, apple, peach, strawberry,
tamarind, tomato and tea
Uses
Trans-2-hexen-1-ol's use in perfumes is somewhat limited.
Lavender and Lavandin oil compositions may
benefit from the topnote created with this alcohol, and certain floral bouquets can be improved with pleasantly green, sweet and
natural notes from the subject material. It
finds increasing use in artificial Geranium
oils.
In flavors, traces are used in fruit complexes,
and it is a common ingredient in artificial
Strawberry. It adds freshness to Mint compositions, and it is often used to reconstitute
the flavor in Orange juice, whose flavor suflers
severely during the processing.
Definition
ChEBI: 2-hexen-1-ol is a primary allylic alcohol that is 2-hexene in which a hydrogen at position 1 has been replaced by a hydroxy group. It has a role as a plant metabolite. It is an alkenyl alcohol and a primary allylic alcohol.
Preparation
The cis-form can be prepared by hydrogenation of cis-2-hexenol, using an aqueous suspension of colloidal palladium;
from cis-4-chloro-2-butenol and magnesium ethyl bromide; the commercial product is a mixture of the cis- and trans-isomers and
can be prepared from propyl vinyl carbinol by heating with aluminum oxide.
Aroma threshold values
Aroma characteristics at 1.0%: fresh, fatty green, tomato vegetative, with leafy, green fruity and herbal
nuances.
Taste threshold values
Taste characteristics at 5 ppm: fresh, leafy green, slightly fatty with grassy, fruity and juicy nuances, tomato
and celery nuances.
