1-Octen-3-OL

Base Information

• Chemical Name: 1-Octen-3-OL
• CAS No.: 3391-86-4
• Deprecated CAS: 50999-79-6
• Molecular Formula: C8H16O
• Molecular Weight: 128.214
• Hs Code.: 29052990
• European Community (EC) Number: 222-226-0
• NSC Number: 87563
• UNII: WXB511GE38
• DSSTox Substance ID: DTXSID3035214
• Nikkaji Number: J34.615B
• Wikipedia: 1-Octen-3-ol
• Wikidata: Q161667
• Metabolomics Workbench ID: 3181
• ChEMBL ID: CHEMBL3183573
• Mol file: 3391-86-4.mol

Synonyms:1-octen-3-ol;1-octen-3-ol, (+-)-isomer;1-octen-3-ol, (R)-isomer;octenol

Chemical Property of 1-Octen-3-OL

Chemical Property:

• Appearance/Colour: Clear colorless to pale yellow liquid
• Vapor Pressure: 0.531mmHg at 25°C
• Melting Point: -49 °C
• Refractive Index: n20/D 1.437(lit.)
• Boiling Point: 168.4 °C at 760 mmHg
• PKA: 14.63±0.20(Predicted)
• Flash Point: 61.1 °C
• PSA: 20.23000
• Density: 0.834 g/cm³
• LogP: 2.11360
• Storage Temp.: Store below +30°C.
• Solubility.: Acetonitrile (Slightly), Chloroform, Ethyl Acetate (Slightly)
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 128.120115130
• Heavy Atom Count: 9
• Complexity: 69

Purity/Quality:

99% ^*data from raw suppliers

(±)-1-Octen-3-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/38-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=C)O
• Description: 1-octen-3-ol, octenol (also known as mushroom alcohol) is a kind of secondary alcohol. It can emit special smell that can attract the biting insects such as mosquitoes. It is contained in the breath and sweat of mammals, and seems to be appreciated by insects such as mosquitoes. It is mainly produced by some plants and fungi including mushrooms and lemon balm through oxidative breakdown of linoleic acid. It can be used in combination with carbon dioxide to attract the insects to kill them. In addition, it can also be used as a food additive and used in certain perfumes. However, in animal study, it could disrupt dopamine homeostasis, and might be potentially involved in Parkinsonism. 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.
• Uses: 1-Octen-3-ol is a chemical that attracts biting insects such as mosquitoes. It occurs naturally in some plants, fungi, and molds; and it is a metabolite of linoleic acid. It is also found in human breath and sweat, which is unfortunate because it attracts mosquitoes and other biting insects and it was once believed that insect repellent DEET works by blocking the insects' octenol odorant receptors. Used as a flavoring agent in cheese and chocolate. Used as a perfuming agent in cosmetic industry. Since the discovery in the early 1980s that 1-octen-3-ol, isolated from oxen breath, attracts tsetse fly, there has been growing interest in exploring the use of this semiochemical as a possible generic lure for trapping host-seeking mosquitoes. Intriguingly, traps baited with 1-octen-3-ol captured significantly more females of the malaria mosquito, Anopheles gambiae, and the yellow fever mosquito, Aedes aegypti, than control traps, but failed to attract the southern house mosquito, Culex quinquefasciatus. (±)-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.

Technology Process of 1-Octen-3-OL

There total 194 articles about 1-Octen-3-OL which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

Toluene-4-sulfonic acid (2R,3R)-3-pentyl-oxiranylmethyl ester (111321-48-3) → (R)-1-octene-3-ol (3391-86-4,3687-48-7,24587-53-9,50999-79-6)

Guidance literature:

With sodium hydroxide; tellurium; sodium formaldehyde sulfoxylate; In tetrahydrofuran; for 6h; Ambient temperature;

DOI:10.1021/jo00055a029

Reference yield: 91.0%

(2R,3R)-2-<(R)-p-tolylsulfinyl>-1-(trimethylsilyl)-3-octanol (155394-02-8) → (R)-1-octene-3-ol (3391-86-4,3687-48-7,24587-53-9,50999-79-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.75h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80816-4

Reference yield: 90.0%

1-pentyl-2-propenyl acetate → (R)-1-octene-3-ol (3391-86-4,3687-48-7,24587-53-9,50999-79-6)

Guidance literature:

1-pentyl-2-propenyl acetate; With potassium carbonate; In methanol; at 20 ℃; for 2h; Inert atmosphere;

With di-isopropyl azodicarboxylate; acetic acid; triphenylphosphine; In methanol; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1002/ejoc.201301365

upstream raw materials:

oct-1-en-3-one

oct-1-en-3-yl acetate

C₂₂H₂₆O

(2R,3S)-2-Iodomethyl-3-pentyl-oxirane

Downstream raw materials:

(+/-)-phthalic acid mono-(1-pentyl-allyl ester)

(R)-octan-3-ol

(S)-2-hydroxyheptanal

(S)-octan-3-ol

Refernces

• 1、 Basavaiah,Bhaskar Raju. "Bovine liver acetone powder (BLAP) catalyzed synthesis of chiral C-8 allyl alcohols: An application of substrate specificity approach". . p. 4137 - 4148. Retrieved 1994.
• 2、 Mihailovic,M.L. et al.. "". . p. 215 - 226. Retrieved 1967.
• 3、 Patel, Pranav,Chang, Chih-Tsung,Kang, Namin,Lee, Gue-Jae,Powell, William S.,Rokach, Joshua. "Reductive deprotection of silyl groups with Wilkinson's catalyst/catechol borane". . p. 5289 - 5292. Retrieved 2007.
• 4、 Chinnabattigalla, Sreenivasulu,Choudhury, Aditya,Gedu, Satyanarayana. "[Pd]-Catalyzedpara-selective allylation of phenols: access to 4-[(E)-3-aryl/alkylprop-2-enyl]phenols". supporting information. p. 8259 - 8263. Retrieved 2021/10/12.
• 5、 Gontala, Arjun,Woo, Sang Kook. "Visible-Light Photoredox-Catalyzed α-Regioselective Conjugate Addition of Allyl Groups to Activated Alkenes". supporting information. p. 3223 - 3228. Retrieved 2020/07/06.