1-Octan-3-ol

1-Octan-3-ol
Compound Structure:
Synonyms: 1-OCTEN-3-OL; Oct-1-en-3-ol;1-Vinylhexanol;Vinyl amyl carbinol;3-Hydroxy-1-octene;Amyl vinyl carbinol;Mushroom alcohol;Pentyl vinyl carbinol;Octen-3-ol;Matsuica alcohol;Vinyl hexanol;Pentylvinylcarbinol;octene-1-ol-3;Oct-1-ene-3-ol
Compound ID: NMPC-110
PubChem ID:

18827

Molecular Formula: C8H16O
Canonical SMILES: CCCCCC(C=C)O
InChIKey: VSMOENVRRABVKN-UHFFFAOYSA-N
About the compound:

Oct-1-en-3-ol is an alkenyl alcohol with a structure based on an unbranched C8 chain featuring the hydroxy group at C-2 and unsaturation at C-1 to C-2. It is a major volatile compound found in numerous mushrooms and fungi. This compound plays multiple roles as an insect attractant, a volatile oil component, a fungal metabolite, and an antimicrobial agent. Oct-1-en-3-ol is classified as an alkenyl alcohol and a fatty alcohol, deriving from the hydride of 1-octene. 1-Octen-3-ol, often referred to as octenol, is a natural compound that can be found in various organisms, including Nepeta nepetella and Origanum syriacum. It is a metabolite produced by Saccharomyces cerevisiae.1-Octen-3-ol is recognized for its role as a chemical that attracts biting  insects like mosquitoes. It is present in human breath and sweat, and it is believed that insect repellents like DEET work by blocking the insects' octenol odorant receptors. This compound exists in two enantiomeric forms, namely (R)-(–)-1-octen-3-ol and (S)-(+)-1-octen-3-ol. Octenol is produced by various plants and fungi, including edible mushrooms and lemon balm, and is formed during the oxidative breakdown of linoleic acid.

Interestingly, octenol can also be a wine fault, defined as a cork taint, and it occurs in wines made with grape bunches contaminated by rot.

GHS Hazard Statements

H302 (96.75%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (99.89%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (99.89%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H332 (97.37%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H400 (94.01%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]


Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

128.21 g/mol

XLogP3-AA

2.6

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

5

Exact Mass

128.120115130 g/mol

Monoisotopic Mass

128.120115130 g/mol

Topological Polar Surface Area

20.2Ų

Heavy Atom Count

9

Formal Charge

0

Complexity

69

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

1

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Colourless oily liquid; powerful sweet earthy odour with strong herbaceous note reminiscent of lavender-lavadin, rose and hay

Boiling Point

84.00 to 85.00 °C. @ 25.00 mm Hg

Melting Point

175 °C

Density

0.835-0.845

Solubility 

insoluble in water; soluble in oils

Source: PubChem

Source Species: Bryophyllum pinnatum
Hyparrhenia rufa
Acalypha segetalis
Luffa cylindrica
Pteris togoensis
Tecoma stans
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