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alpha-methyl cinnamyl alcohol

Alpha-methyl cinnamyl alcohol is a fragrance agent characterized by a medium-strength sweet balsamic odor, used primarily in perfuming with notable stability and safety profiles.
Chemical Structure

General Material Description

Alpha-methyl cinnamyl alcohol (PubChem CID 6393846) is an aromatic alcohol belonging to the class of unsaturated phenylpropenols with the molecular formula C10H12O. This colorless to pale liquid exhibits a characteristic sweet balsamic odor reminiscent of styrax and oriental notes. Also known by several synonyms such as 3-buten-2-ol, (E)-4-phenyl-, and methyl styryl carbinol, it is typically derived through synthetic organic processes. The compound finds its primary role in fragrance compositions where its distinctive scent profile enhances oriental, balsam, and floral accords.

Occurrence, Applicability & Potential Uses

Alpha-methyl cinnamyl alcohol occurs predominantly in synthetic form as it is not widely present in natural sources. It is applied extensively in the fragrance industry due to its appealing sweet balsamic and oriental aroma. Under IFRA (Global) standards, it is approved for limited use in perfuming agents with restrictions on maximum concentration to ensure consumer safety. Its olfactory characteristics make it suitable for blending in fragrances that evoke lily of the valley, spices, and warm balsam notes, fulfilling roles in both fine fragrances and personal care products.

Physico-Chemical Properties Summary

The compound displays moderate volatility with a boiling point range between 288 to 289°C at standard atmospheric pressure and a low vapor pressure of 0.004 mmHg at 25°C, indicating relatively low evaporation rates under ambient conditions. Its estimated logP of 1.929 suggests balanced lipophilicity favoring solubility in organic solvents like alcohol, while it exhibits limited water solubility. The flash point is approximately 93°C, reflecting its flammability risk under elevated temperatures. These properties influence its formulation in fragrance mixtures by contributing to sustained aroma release and substantivity, typically lasting up to 48 hours when applied at full strength.

FAQ

What is alpha-methyl cinnamyl alcohol and how is it used?
Alpha-methyl cinnamyl alcohol is a synthetic aromatic alcohol used primarily as a fragrance ingredient. It carries a medium-strength sweet balsamic and oriental odor useful in perfumery. Its scent profile supports applications that require warm, floral, and spicy fragrance accents. The compound is incorporated into various fine fragrances and personal care products to enhance aromatic complexity.
Where does alpha-methyl cinnamyl alcohol occur and what are its regulatory considerations?
This compound is not commonly found in nature and is generally produced synthetically. Regulatory oversight, such as the IFRA (Global) standards, governs its use in fragrances to ensure consumer safety. Usage limits are defined, for example, a maximum of 0.01% in fine fragrances applied dermally and up to 8% in fragrance concentrates. These guidelines address possible skin irritation risks despite the compound's low toxicity profile.
What safety information is relevant for handling alpha-methyl cinnamyl alcohol?
Alpha-methyl cinnamyl alcohol is classified as an irritant to skin and eyes. According to European safety data sheets, precautions include avoiding direct contact and using protective clothing. Toxicological studies indicate a low acute toxicity with oral LD50 around 2400 µL/kg in rats and dermal LD50 exceeding 5000 mg/kg in rabbits. The compound is not approved for flavor use and should be handled following recommended exposure guidelines to minimize irritation.

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
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2906.29.6000
ChemSpider:View

General Material Information

Preferred name alpha-methyl cinnamyl alcohol
Trivial Name 2-Methyl-3-phenyl-2-propen-1-ol
Short Description 3-buten-2-ol, (E)-4-phenyl-
Formula C10 H12 O
CAS Number 1504-55-8
ECHA Number 216-128-7
FDA UNII E7JPK3PRD9
Nikkaji Number G3K19216O
Beilstein Number 2040727
MDL MFCD00004738
xLogP3-AA 2.30 (est)
NMR Predictor External link
Synonyms
  • 3-buten-2-ol, (E)-4-phenyl-
  • cypriol
  • alpha- methyl cinnamic alcohol
  • methyl styryl carbinol
  • 2-methyl-3-phenyl-2-propen-1-ol
  • alpha- methyl-3-phenyl-2-propen-1-ol
  • trans-2-methyl-3-phenyl-2-propen-1-ol
  • (E)-2-methyl-3-phenylprop-2-en-1-ol
  • a- methylcinnamic alcohol
  • alpha- methylcinnamyl alcohol
  • 3-phenyl-2-methyl-propen-2-ol-1
  • (3E)-4-phenyl-3-buten-2-ol
  • (E)-4-phenyl-3-buten-2-ol
  • (E)-2-methyl-3-phenylprop-2-en-1-ol
  • 2-Propen-1-ol, 2-methyl-3-phenyl-
  • 2-Methyl-3-phenyl-2-propen-1-ol
  • α-Methylcinnamyl alcohol
  • 2-Methyl-3-phenyl-2-propenol

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 148.20483398438
Boiling Point 288 to 289°C @ 760 mm Hg
Vapor Pressure 0.004 mmHg @ 25 °C
Flash Point TCC Value 93.33 °C TCC
logP (o/w) 1.929 est
Solubility
alcohol Yes
water, 2274 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Balsamic
sweet, balsamic, floral, oriental, storax
Odor strength medium
Substantivity 48 hour(s) at 100.00 %
General comment At 100.00 %. sweet balsam floral oriental styrax

Potential Uses

Applications
Odor purposes Balsam , Lily of the valley , Oriental , Spice
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
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.
Human Experience:
2 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 2400 ul/kg
Food and Cosmetics Toxicology. Vol. 13, Pg. 851, 1975.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 13, Pg. 851, 1975.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
maximum skin levels for fine fragrances:
0.0100 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2004)
Recommendation for alpha-methyl cinnamyl alcohol usage levels up to:
8.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics:
0.2000 %
Dermal Systemic Exposure in Cosmetic Products:
0.0051 mg/kg/day (IFRA, 2004)
Recommendation for alpha-methyl cinnamyl alcohol flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):1504-55-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6393846
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
(E)-2-methyl-3-phenylprop-2-en-1-ol
Chemidplus:0001504558
RTECS:GE2340000 for cas# 1504-55-8