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(S)-1-octen-3-ol

(S)-1-octen-3-ol is a naturally occurring alcohol noted for its earthy, mushroom-like odor, widely used as a flavor and fragrance agent.

General Material Description

(S)-1-octen-3-ol is a chiral alcohol with the molecular formula C8H16O and an approximate molecular weight of 128.21 g/mol. It appears as a colorless to pale yellow liquid and offers a distinct earthy, mushroom-like aroma. Commonly known as (S)-matsutake alcohol or (S)-mushroom alcohol, this compound is a key contributor to the characteristic odor of certain fungi. The chemical links to its profile are accessible via CHEBI:46735. It is typically isolated or synthesized for use in flavor and fragrance applications, leveraging its natural origin to recreate or enhance earthy and fungal notes in formulations.

Occurrence, Applicability & Potential Uses

(S)-1-octen-3-ol naturally occurs in various mushroom species, contributing significantly to their distinctive aroma. It is a biologically relevant volatile organic compound produced during fungal metabolism. Industrially, it finds application as a flavor and fragrance agent, valued for imparting earthy, green, and mushroom-like sensory characteristics to products. Its use is recognized within the flavor and fragrance sectors, following safety and quality standards. Regulatory frameworks such as IFRA (Global) provide guidance on its incorporation levels in consumer goods, ensuring its appropriate and safe utilization.

Physico-Chemical Properties Summary

(S)-1-octen-3-ol exhibits a moderate vapor pressure of approximately 0.531 mmHg at 25°C, indicating a balance between volatility and persistence in formulations. Its flash point is estimated around 68°C (154°F), reflecting considerations for storage and handling safety. The compound demonstrates limited solubility in water at about 1836 mg/L, sufficient to influence its dispersion in aqueous-based products. The estimated logP value near 2.5 highlights moderate lipophilicity, affecting its interaction with lipid media and influencing how it is incorporated into complex flavor and fragrance matrices. These properties contribute decisively to its performance and stability during product formulation.

FAQ

What is (S)-1-octen-3-ol and what are its main properties?
(S)-1-octen-3-ol is a chiral alcohol recognized for its earthy and mushroom-like odor. It has the molecular formula C8H16O with a molecular weight of approximately 128.21 g/mol. This compound is a colorless to pale yellow liquid with moderate volatility and limited water solubility. Its sensory profile makes it valuable in flavor and fragrance applications where natural, earthy notes are desired.
Where does (S)-1-octen-3-ol occur naturally, and how is it used industrially?
(S)-1-octen-3-ol is naturally found in various mushroom species and arises from fungal metabolic processes. It contributes significantly to the characteristic mushroom odor. Industrial use focuses on incorporating it as a flavor and fragrance agent in products requiring earthy and green aroma notes. Its inclusion in formulations is guided by regulatory standards like IFRA (Global) to ensure appropriate exposure levels.
What safety and regulatory frameworks apply to (S)-1-octen-3-ol in flavor and fragrance use?
Extensive safety evaluations indicate that (S)-1-octen-3-ol is generally regarded as safe under typical usage concentrations, with no specific hazard classifications under OSHA (US) guidelines. Regulatory bodies such as IFRA (Global) provide codes of practice governing its permissible rates in consumer products. Additionally, materials safety data sheets and resources like RIFM offer assessments supporting its careful and controlled use within flavor and fragrance industries.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

General Material Information

Trivial Name (S)-1-octen-3-ol
Short Description (S)-matsutake alcohol
Formula C8 H16 O
CAS Number 24587-53-9
FDA UNII 07D31239FH
Nikkaji Number J66.869I
Beilstein Number 1720731
MDL MFCD04972323
xLogP3-AA 2.60 (est)
NMR Predictor External link
Synonyms
  • (S)- amyl vinyl carbinol
  • (S)- matsutake alcohol
  • (S)- mushroom alcohol
  • (3S)- oct-1-en-3-ol
  • (S)-(+)-1-octen-3-ol
  • (S)- pentyl vinyl carbinol
  • (S)-1-vinyl hexanol

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 128.21472167969
Vapor Pressure 0.531 mmHg @ 25 °C
Flash Point TCC Value 68 °C TCC
logP (o/w) 2.519 est
Solubility
water, 1836 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Earthy
moldy, grassy, herbal, green, musty
General comment At 1.00 % in dipropylene glycol. moldy grassy herbal green musty

Safety Information

Safety information

Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :2724898
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(3S)-oct-1-en-3-ol
Chemidplus:0024587539