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(S)-styralyl alcohol
(S)-styralyl alcohol is a chiral aromatic alcohol known for its floral odor, commonly applied as a flavor and fragrance agent.
General Material Description
(S)-styralyl alcohol, also known as (S)-1-phenylethanol, is a chiral aromatic alcohol with molecular formula C8H10O. It appears as a liquid with a distinct floral odor reminiscent of hyacinth, gardenia, and strawberry. This compound belongs to the family of phenyl ethanol derivatives and carries a characteristic optical rotation ranging from -46 to -40 degrees, indicating its stereochemical purity. It is listed under several synonyms including (S)-(-)-α-methylbenzyl alcohol and (S)-phenylmethylcarbinol. Produced by various synthetic and biotechnological methods, (S)-styralyl alcohol is commonly sourced for its olfactory attributes. The compound is indexed in controlled vocabularies such as ChEBI under identifier CHEBI:16346.
Occurrence, Applicability & Potential Uses
(S)-styralyl alcohol occurs naturally in some plant extracts and is biosynthesized as part of secondary metabolic pathways in various organisms. Its pronounced floral odor makes it valuable in fragrance design and flavor formulation. The compound’s incorporation into perfumes, cosmetics, and food flavoring agents is well-documented, benefiting from its pleasant and distinctive aromatic profile. Regulatory standards covering its use include IFRA (International Fragrance Association) guidelines, which govern safe concentration limits in consumer products worldwide. (S)-styralyl alcohol also serves as an intermediate in organic synthesis, delivering chirality and aromatic character.
Physico-Chemical Properties Summary
(S)-styralyl alcohol is a moderately volatile liquid with a boiling range between 206 and 207 °C at atmospheric pressure and a flash point estimated at 85 °C (185 °F). The specific gravity spans from 1.011 to 1.015 at 20 °C, and its refractive index lies between 1.526 and 1.53 at the same temperature. It displays an optical rotation from -46 to -40 degrees, confirming its stereochemical configuration. The compound exhibits moderate lipophilicity, with an estimated logP of 1.382. Solubility data indicate good miscibility with alcohol and appreciable water solubility near 19.54 g/L at 25 °C. Vapor pressure is relatively low, measured at 0.139 mmHg at 25 °C, suggesting limited volatility under ambient conditions, affecting its formulation behavior in flavor and fragrance matrices.
FAQ
What is (S)-styralyl alcohol and what are its primary characteristics?
(S)-styralyl alcohol is a chiral aromatic alcohol known chemically as (S)-1-phenylethanol. It is characterized by a floral scent with notes of hyacinth, gardenia, and strawberry. This compound has the molecular formula C8H10O and features stereospecific optical activity. It typically appears as a liquid with a boiling point near 206 to 207 °C and displays solubility in both alcohol and water. These properties contribute to its common application as a flavor and fragrance ingredient.
How is (S)-styralyl alcohol used, and where is it commonly found?
(S)-styralyl alcohol is widely utilized in the flavor and fragrance industry due to its appealing floral aroma. It occurs naturally in certain plants and can be synthesized industrially. It is incorporated into perfumes, cosmetics, and food flavorings to impart floral and fresh notes. The compound also functions as a chiral building block in organic synthesis. Its moderate volatility and good solubility facilitate formulation in various product types.
What regulations and safety information apply to (S)-styralyl alcohol?
(S)-styralyl alcohol is subject to safety assessments such as those by RIFM and regulated under the IFRA Code of Practice (Global), which establishes usage limits in perfumery and related applications. Standard safety data sheets report no significant hazard classifications under OSHA’s Hazard Communication Standard (29 CFR 1910). Toxicological data remain limited but show no noted acute hazards. It is generally considered safe within established concentration limits. Comprehensive regulatory information can be found via agencies such as the EPA and FDA using its CAS number 1445-91-6.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
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| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| Leffingwell: | Chirality or Article |
| (1S)-1-phenylethanol | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 443135 |
| Pubchem (sid): | 135078473 |
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 |
| CHEMBL: | View |
| KEGG (GenomeNet): | C11348 |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2906.29.6000 |
| ChemSpider: | View |
General Material Information
| Preferred name | (S)-styralyl alcohol |
| Trivial Name | (S)-1-Phenylethanol |
| Short Description | benzenemethanol, a-methyl-, (aS)- |
| Formula | C8 H10 O |
| CAS Number | 1445-91-6 |
| FDA UNII | 2MIC4QLY2X |
| Nikkaji Number | J56.778G |
| Beilstein Number | 2039797 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 122.16690063477 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 8.422 to 8.456 |
| Refractive Index | 1.526 to 1.53 @ 20 °C |
| Optical Rotation | -46 to -40 |
| Boiling Point | 206 to 207°C @ 760 mm Hg |
| Vapor Pressure | 0.139 mmHg @ 25 °C |
| Flash Point TCC Value | 85 °C TCC |
| logP (o/w) | 1.382 est |
| Solubility | |
| alcohol | Yes |
| water, 1.954e+004 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Floral | |
| hyacinth, gardenia, strawberry | |
| General comment | At 100.00 %. hyacinth gardenia strawberry |
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 :443135 |
| National Institute of Allergy and Infectious Diseases:Data |
| (1S)-1-phenylethanol |
| Chemidplus:0001445916 |
| RTECS:DO9275000 for cas# 1445-91-6 |