3391-86-4 Usage
Description
1-Octen-3-ol, also known as mushroom alcohol, is a secondary alcohol that occurs naturally in mushrooms and is produced by certain plants and fungi. It has a powerful, sweet, earthy odor with a strong herbaceous note reminiscent of lavender, rose, and hay. It is a potent mosquito attractant and is also found in human breath and sweat, which attracts biting insects.
Uses
Used in Flavor Industry:
1-Octen-3-ol is used as a flavoring agent for various food products, including cheese, potato, savory, asparagus, carrot, cucumber, and mushroom, due to its mushroom, green, vegetable, and fatty odor.
Used in Perfume Industry:
1-Octen-3-ol is used as a perfuming agent in the cosmetic industry, particularly in lavender compositions and mushroom aromas.
Used in Insect Control:
1-Octen-3-ol is used in combination with carbon dioxide to attract insects, such as mosquitoes, in order to kill them. It has been shown to interfere with dopamine transport in the brain of fruit flies, suggesting its potential involvement in parkinsonism.
Used in Insect Trapping:
Since its discovery as a mosquito attractant, there has been growing interest in exploring the use of 1-octen-3-ol as a possible generic lure for trapping host-seeking mosquitoes, particularly female Anopheles gambiae and Aedes aegypti.
Used in Food and Beverage Industry:
1-Octen-3-ol is used in edible flavor blends for various food and beverages, such as tomato, milk, and nut, due to its sweet, herbaceous taste and intense mushroom, forest-earthy odor.
Natural Occurrence:
1-Octen-3-ol is 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, and winter savory.
Chemical Properties:
1-Octen-3-ol is a colorless to yellow liquid with a mushroom, green, vegetable, and fatty odor. It is an unsaturated alcohol that exists as two enantiomers, the (R)-(–)-form and the (S)-(+)-form, and is most often found as a racemic mixture. It has a powerful, sweet, earthy odor with a strong herbaceous note and a sweet, herbaceous taste.
References
http://www.chm.bris.ac.uk/motm/octenol/octenolh.htm
https://en.wikipedia.org/wiki/1-Octen-3-ol
Preparation
From magnesium amyl bromide and acrolein.
Flammability and Explosibility
Notclassified
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.
Check Digit Verification of cas no
The CAS Registry Mumber 3391-86-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,3,9 and 1 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 3391-86:
(6*3)+(5*3)+(4*9)+(3*1)+(2*8)+(1*6)=94
94 % 10 = 4
So 3391-86-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3/t8-/m0/s1
3391-86-4Relevant articles and documents
A cascade aerobic epoxidation of alkenes over Au/CeO2 and Ti-mesoporous material by "in situ" formed peroxides
Aprile, Carmela,Corma, Avelino,Domine, Marcelo E.,Garcia, Hermenegildo,Mitchell, Chris
, p. 44 - 53 (2009)
The one-pot epoxidation of alkenes with O2 is performed with nano-particulated Au/CeO2 and Ti-MCM-41 silylated materials in the presence of a hydrocarbon and azobis-iso-butyronitrile (AIBN) as a promoter. This initiator is able to fo
Badenhop,Wilkens
, p. 179 (1969)
Tsuji,Mandai
, p. 975 (1977)
[Pd]-Catalyzedpara-selective allylation of phenols: access to 4-[(E)-3-aryl/alkylprop-2-enyl]phenols
Chinnabattigalla, Sreenivasulu,Choudhury, Aditya,Gedu, Satyanarayana
supporting information, p. 8259 - 8263 (2021/10/12)
4-[(E)-3-Arylprop-2-enyl]phenols are omnipresent scaffolds and constitute natural products and biologically significant compounds. Obtusastyrene and obtustyrene are two such phenolic-based natural products isolated fromDalbergia retusa. The development of strategies based on a site-selective allylation, particularly protecting group-free substrates and non-activated coupling agents, is indispensable in organic synthesis. Herein, we present a highly regioselective [Pd]-catalyzedpara-allylation of phenols using simple, inactivated allylic alcohols as allylating coupling partners. Notably, this strategy is successful in open-air and under mild reaction conditions. Besides, the efficacy of the present protocol was demonstrated by the direct synthesis of obtusastyrene and obtustyrene.
Concise, scalable and enantioselective total synthesis of prostaglandins
Zhang, Fuhao,Zeng, Jingwen,Gao, Mohan,Wang, Linzhou,Chen, Gen-Qiang,Lu, Yixin,Zhang, Xumu
, p. 692 - 697 (2021/06/01)
Prostaglandins are among the most important natural isolates owing to their broad range of bioactivities and unique structures. However, current methods for the synthesis of prostaglandins suffer from low yields and lengthy steps. Here, we report a practicability-oriented synthetic strategy for the enantioselective and divergent synthesis of prostaglandins. In this approach, the multiply substituted five-membered rings in prostaglandins were constructed via the key enyne cycloisomerization with excellent selectivity (>20:1 d.r., 98% e.e.). The crucial chiral centre on the scaffold of the prostaglandins was installed using the asymmetric hydrogenation method (up to 98% yield and 98% e.e.). From our versatile common intermediates, a series of prostaglandins and related drugs could be produced in two steps, and fluprostenol could be prepared on a 20-gram scale. [Figure not available: see fulltext.]
Palladium-catalyzed regioselective synthesis of B(4,5)-or B(4)-substituted: O-carboranes containing α,β-unsaturated carbonyls
Li, Jiaoyi,Lu, Jian,Tian, Song,Wang, Qian,Zhang, Chuyi,Zhang, Jianwei,Zhou, Ling
supporting information, p. 4723 - 4727 (2020/07/13)
With the help of a carboxylic acid directing group, Pd-catalyzed regioselective synthesis of B(4,5)-or B(4)-substituted o-carboranes containing α,β-unsaturated carbonyls has been reported. The-COOH, removed during the course of the reaction, is responsible for controlling the regioselectivity. The desired products could be obtained in moderate to good yields.