1-phenyl propyl alcohol
1-phenyl-1-propanol
Identification
| Name | 1-phenyl propyl alcohol |
| IUPAC | 1-phenylpropan-1-ol |
| CAS Number | 93-54-9 |
| EINECS | 202-256-0 |
| FDA UNII | 0F897O3O4M |
| Molecular Formula | C9 H12 O |
| Molecular Weight | 136.19384000 |
| MDL Number | MFCD00004564 |
| Nikkaji Number | J4.678G |
| Beilstein | 1906759 |
| CoE Number | 82 |
| XlogP3 | 1.90 (est) |
Regulatory
| JECFA Food Flavoring | 822 1-phenyl-1-propanol |
| DG SANTE Food Flavourings | 02.033 1-phenylpropan-1-ol |
| FEMA Number | 2884 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 93-54-9 ; 1-PHENYL-1-PROPANOL |
| FDA Regulation | FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION |
Physical Properties
| Appearance | colorless to pale yellow clear oily liquid (est) |
| Assay | 97.00 to 100.00 |
| Additional Assay Information | racemate |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.99300 to 1.00000 @ 25.00 °C. |
| Pounds per Gallon - (est). | 8.263 to 8.321 |
| Refractive Index | 1.51700 to 1.52200 @ 20.00 °C. |
| Boiling Point | 103.00 °C. @ 14.00 mm Hg, 219.00 to 220.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.071000 mmHg @ 25.00 °C. (est) |
| Flash Point | 195.00 °F. TCC ( 90.56 °C. ) |
| logP (o/w) | 1.919 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Organoleptic Properties
| Odor Description | at 100.00 %. |
| Taste Description | balsam honey |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | gavage-rat LD50 2800 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 > 2000 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Recommendation for 1-phenyl propyl alcohol usage levels up to | 0.6000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.24 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | 0.10 (μg/capita/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| baked goods | - |
| beverages(nonalcoholic) | - |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | - |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | - |
| fruit ices | - |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | - |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | - |
| soft candy | - |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
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Potential Uses
Natural Occurrence
Synonyms
benzenemethanol, a-ethyl-
bilergon
carbicol
choleda
ejibil
epatoxfen
alpha-
ethyl benzene methanol
alpha-
ethyl benzyl alcohol
ethyl phenyl carbinol
a-
ethylbenzenemethanol
(±)-a-
ethylbenzyl alcohol
a-
ethylbenzyl alcohol
ethylphenylcarbinol
felicur
felitrope
fepar
gallenperlen
alpha-
hydroxypropyl benzene
livonal
phenyl cholon
phenyl ethyl carbinol
1-
phenyl propan-1-ol
1-
phenyl propanol
1-
phenyl-1-hydroxypropane
1-
phenyl-1-propanol
1-
phenylpropan-1-ol
1-
phenylpropanol
1-
phenylpropyl alcohol
propan-1-ol, 1-phenyl-
unichol
PubMed:
NBO, conformational, NLO, HOMO-LUMO, NMR and electronic spectral study on 1-phenyl-1-propanol by quantum computational methods.
PubMed:
Optical resolution of aromatic alcohols using silica nanoparticles grafted with helicene.
PubMed:
Density functional theory studies on the inclusion complexes of cyclic decapeptide with 1-phenyl-1-propanol enantiomers.
PubMed:
Optimization of lipase-catalyzed enantioselective production of 1-phenyl 1-propanol using response surface methodology.
PubMed:
Kinetic resolution of racemic 1-phenyl 1-propanol by lipase catalyzed enantioselective esterification reaction.
PubMed:
Comparison of chiral electrophoretic separation methods for phenethylamines and application on impurity analysis.
PubMed:
Asymmetric synthesis of (S)-3-chloro-1-phenyl-1-propanol using Saccharomyces cerevisiae reductase with high enantioselectivity.
PubMed:
Halonium ion-assisted deiodination of styrene-based vicinal iodohydrins followed by rearrangement through phenyl migration.
PubMed:
Antagonism of human adiponectin receptors and their membrane progesterone receptor paralogs by TNFalpha and a ceramidase inhibitor.
PubMed:
Effects of ceramide, ceramidase inhibition and expression of ceramide kinase on cytosolic phospholipase A2alpha; additional role of ceramide-1-phosphate in phosphorylation and Ca2+ signaling.
PubMed:
Dual DAT/sigma1 receptor ligands based on 3-(4-(3-(bis(4-fluorophenyl)amino)propyl)piperazin-1-yl)-1-phenylpropan-1-ol.
PubMed:
Antidepressant-like pharmacological profile of a novel triple reuptake inhibitor, (1S,2S)-3-(methylamino)-2-(naphthalen-2-yl)-1-phenylpropan-1-ol (PRC200-SS).
PubMed:
Experimental probing and modeling of key sorbent-solute interactions of norephedrine enantiomers with polysaccharide-based chiral stationary phases.
PubMed:
Analysis of the mechanism of asymmetric amplification by chiral auxiliary trans-1,2-diaminocyclohexane bistriflamide.
PubMed:
Modulation of ceramide metabolism in T-leukemia cell lines potentiates apoptosis induced by the cationic antimicrobial peptide bovine lactoferricin.
PubMed:
Polymer supported naphthalene-catalysed sodium reactions.
PubMed:
Conformational preferences of chiral molecules: free jet rotational spectrum of 1-phenyl-1-propanol.
PubMed:
Oxovanadium(V) tetrathiacalix[4]arene complexes and their activity as oxidation catalysts.
PubMed:
De novo C16- and C24-ceramide generation contributes to spontaneous neutrophil apoptosis.
PubMed:
Enantioseparation of 1-phenyl-1-propanol on cellulose-derived chiral stationary phase by supercritical fluid chromatography II. Non-linear isotherm.
PubMed:
Oxidations of secondary alcohols to ketones using easily recyclable bis(trifluoroacetate) adducts of fluorous alkyl iodides, CF3(CF2)(n-1)I(OCOCF3)2.
PubMed:
New chiral Schiff base as a tridentate ligand for catalytic enantioselective addition of diethylzinc to aldehydes.
PubMed:
Excitation, ionization, and fragmentation of chiral molecules in asymmetric microenvironments: a mass-resolved R2PI spectroscopic study.
PubMed:
Apoptosis induced by intracellular ceramide accumulation in MDA-MB-435 breast carcinoma cells is dependent on the generation of reactive oxygen species.
PubMed:
Enantioseparation of secondary alcohols by diastereoisomeric salt formation.
PubMed:
Chiral clusters in a supersonic beam: R2PI-TOF spectroscopy of diastereomeric carboxylic esters/(R)-(+)-1-phenyl-1-propanol complexes.
PubMed:
Enantioseparation of 1-phenyl-1-propanol by supercritical fluid-simulated moving bed chromatography.
PubMed:
Enantioseparation of 1-phenyl-1-propanol on Chiralcel OD by supercritical fluid chromatography. I. Linear isotherm.
PubMed:
Ceramide enhances acrosomal exocytosis triggered by calcium and the calcium ionophore A23187 in boar spermatozoa.
PubMed:
Chiral ligands derived from Abrine 8. An experimental and theoretical study of free ligand conformational preferences and the addition of diethylzinc to benzaldehyde.
PubMed:
Sphingosine-dependent apoptosis: a unified concept based on multiple mechanisms operating in concert.
PubMed:
Complex formation equilibria of some aromatic beta-amino-alcohols.
PubMed:
Overcoming resistance to gamma-rays in squamous carcinoma cells by poly-drug elevation of ceramide levels.
PubMed:
Highly efficient chiral metal cluster systems derived from Ru3(CO)12 and chiral diiminodiphosphines for the asymmetric transfer hydrogenation of ketones.
PubMed:
Numerical determination of the competitive isotherm of enantiomers.
PubMed:
Chiral discrimination of 2,3-butanediols by laser spectroscopy.
PubMed:
A silica gel-supported ruthenium complex of 1,4,7-trimethyl-1,4,7-triazacyclononane as recyclable catalyst for chemoselective oxidation of alcohols and alkenes by tert-butyl hydroperoxide.
PubMed:
Application of the general rate model and the generalized Maxwell-Stefan equation to the study of the mass transfer kinetics of a pair of enantiomers.
PubMed:
ABT-866, a novel alpha(1A)-adrenoceptor agonist with antagonist properties at the alpha(1B)- and alpha(1D)-adrenoceptor subtypes.
PubMed:
Optimization of catalyst enantioselectivity and activity using achiral and meso ligands.
PubMed:
Study of the adsorption equilibria of the enantiomers of 1-phenyl-1-propanol on cellulose tribenzoate using a microbore column.
PubMed:
Bcl-2 overexpression prevents apoptosis induced by ceramidase inhibitors in malignant melanoma and HaCaT keratinocytes.
PubMed:
Transient relaxation of rat mesenteric microvessels by ceramides.
PubMed:
Nerve growth factor-induced p75-mediated death of cultured hippocampal neurons is age-dependent and transduced through ceramide generated by neutral sphingomyelinase.
PubMed:
Modeling of the separation of the enantiomers of 1-phenyl-1-propanol on cellulose tribenzoate.
PubMed:
Residue size at position 87 of cytochrome P450 BM-3 determines its stereoselectivity in propylbenzene and 3-chlorostyrene oxidation.
PubMed:
Immobilization of chiral ligands on polymer fibers by electron beam induced grafting and applications in enantioselective catalysis.
PubMed:
Resolution and synthesis of optically active alcohols with immobilized ovalbumin and pea protein as new bio-catalysts.
PubMed:
Possible involvement of ceramide in the regulation of rat Leydig cell function.
PubMed:
Enantioseparation of 1-phenyl-1-propanol by simulated moving bed under linear and nonlinear conditions.
PubMed:
Adsorption behavior and prediction of the band profiles of the enantiomers of 3-chloro-1-phenyl-1-propanol. Influence of the mass transfer kinetics.
PubMed:
Study of the adsorption behavior of the enantiomers of 1-phenyl-1-propanol on a cellulose-based chiral stationary phase.
PubMed:
Short-range interactions within molecular complexes formed in supersonic beams: structural effects and chiral discrimination
PubMed:
(1R,2S)-2-[N-methyl-N-(4-toluene-sulfonyl)amino]-1-phenylpropan-1-ol.
PubMed:
Effect of N-acetylsphingosine (C2) and the ceramidase inhibitor (1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol on the regulation of Sertoli cell function.
PubMed:
Role of sphingosine 1-phosphate in the mitogenesis induced by oxidized low density lipoprotein in smooth muscle cells via activation of sphingomyelinase, ceramidase, and sphingosine kinase.
PubMed:
Studies on the interactions of chiral secondary alcohols with rat hydroxysteroid sulfotransferase STa.
PubMed:
(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol as an inhibitor of ceramidase.
PubMed:
Photochemical and photobiological properties of ketoprofen associated with the benzophenone chromophore.
PubMed:
Ceramide-mediated biology. Determination of structural and stereospecific requirements through the use of N-acyl-phenylaminoalcohol analogs.
PubMed:
Benzylic alcohols as stereospecific substrates and inhibitors for aryl sulfotransferase.
PubMed:
Stereospecific metabolic reduction of ketones.
PubMed:
The effects of cofactor and species differences on the in vitro metabolism of propiophenone and phenylacetone.
PubMed:
Electron-capture GLC determination of pseudoephedrine in serum.
PubMed:
Comparison of antimicrobial activity of nuclear-substituted aromatic esters of 5-dimethylamino-1-phenyl-3-pentanol and 3-dimethylamino-1-phenyl-1-propanol with related cyclic analogs.
PubMed:
[Effect of compound 921 C (1-cyclohexyl-3-diethylamino-1-phenyl-1-propanol ethiodide) on gastric secretion and gastrointestinal motility].
PubMed:
Synthesis of 2-amino-1-phenyl-1-propanol and its methylated derivatives.