1-Octen-3-ol

Description

l-Octen-3-ol has a powerful, sweet, earthy odor with a strong, herbaceous note reminiscent of lavender-lavandin, rose, and hay. It has a sweet, herbaceous taste. May be prepared from magnesium amyl bromide and acrolein.

Chemical properties

1-Octen-3-ol may occur in the optically active form. It is found, for example, in lavender oil and is a steam-volatile component of mushrooms. l-Octen-3-ol is a liquid with an intense mushroom, forest–earthy odor that can be prepared by a Grignard reaction from vinylmagnesium bromide and hexanal. It is used in lavender compositions and in mushroom aromas.

Chemical properties

1-Octen-3-ol has a powerful, sweet, earthy odor with a strong, herbaceous note reminiscent of lavender–lavandin, rose and hay. It has a sweet, herbaceous taste.

Occurrence

Originally reported found in the mushroom Armillaria matsutake, a parasite growing on the radical hairs of Pinus densiflora in the forests of Japan; it has been isolated also in the essential oils of Mentha pulegium L., lavender and Mentha timjia. Also reported found in over 160 foods and beverages including banana, kumquat peel oil, berries, currants, guava, grapes, raisin, melon, pineapple, asparagus, potato, tomato, Mentha oils, thyme, wheat bread, cheeses, buttermilk, boiled egg, fish, cooked meats, hop oil, beer, cognac, rum, grape wines, cocoa, coffee, tea, pecans, plum, oats, soybean, olive, cloudberry, plums, beans, mushroom, marjoram, starfruit, sesame seed, fig, kelp, rice, beans, litchi, calamus, dill, licorice, pumpkin, buckwheat, sweet corn, corn tortilla, malt, rice, wort, krill, rosemary, Bourbon vanilla, mountain papaya, endive, lemon balm, shrimp, oyster, crab, clam, scallop, truffle, winter savory, anise hyssop and maté.

The Uses of 1-Octen-3-ol

(±)-1-Octen-3-ol, is one of the volatiles responsible for mold`s odor. It can be used in combination with carbon dioxide to attract insects in order to kill them. In animal study, 1-Octen-3-ol has been shown to interfere with dopamine transport in the brain of fruit flies, so it might be an environmental agent involved in parkinsonism.

Definition

ChEBI: An alkenyl alcohol with a structure based on a C8 unbranched chain with the hydroxy group at C-2 and unsaturation at C-11C-2.

Preparation

From magnesium amyl bromide and acrolein.

Aroma threshold values

Detection: 14 ppb; recognition: 25 ppb

Taste threshold values

Taste characteristics at 10 ppm: mushroom, earthy, fungal, green, oily, vegetative, umami sensation and savory-brothy.

General Description

1-Octen-3-ol occurs naturally in mushrooms. It is the most prominent odor volatile produced by fungi such as Aspergillus, Penicillium and Fusarium species. 1-Octen-3-ol is also formed in major quantity when soybeans are soaked in water as a pretreatment before soymilk production. It is also a potent mosquito attractant.

Flammability and Explosibility

Not classified

Trade name

Matsutakeol (Takasago).

Biochem/physiol Actions

Taste at 0.01-0.20 ppm

Safety Profile

Poison by ingestion and intravenous routes. Moderately toxic by skin contact. When heated to decomposition it emits acrid smoke and irritating fumes.