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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 18:43:05 UTC

Update Date

2023-02-21 17:23:47 UTC

HMDB ID

HMDB0033944

Secondary Accession Numbers

HMDB33944

Metabolite Identification

Common Name

2-Phenylethanol

Description

2-Phenylethanol, also known as benzeneethanol or benzyl carbinol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 2-Phenylethanol exists in all living species, ranging from bacteria to humans. 2-Phenylethanol is a bitter, floral, and honey tasting compound. 2-Phenylethanol is found, on average, in the highest concentration within a few different foods, such as red wines, black walnuts, and white wines and in a lower concentration in grape wines, sweet basils, and peppermints. 2-Phenylethanol has also been detected, but not quantified, in several different foods, such as asparagus, allspices, fruits, horned melons, and lemons. 2-Phenylethanol, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, pervasive developmental disorder not otherwise specified, and autism. 2-phenylethanol has also been linked to the inborn metabolic disorder celiac disease. A primary alcohol that is ethanol substituted by a phenyl group at position 2.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Hydroxyethylbenzene	ChEBI
2-PEA	ChEBI
2-PHENYL-ethanol	ChEBI
Benzeneethanol	ChEBI
Benzylmethanol	ChEBI
beta-PEA	ChEBI
beta-Phenethyl alcohol	ChEBI
beta-Phenylethanol	ChEBI
beta-Phenylethyl alcohol	ChEBI
Phenethyl alcohol	ChEBI
Phenylethyl alcohol	ChEBI
b-PEA	Generator
Β-pea	Generator
b-Phenethyl alcohol	Generator
Β-phenethyl alcohol	Generator
b-Phenylethanol	Generator
Β-phenylethanol	Generator
b-Phenylethyl alcohol	Generator
Β-phenylethyl alcohol	Generator
1-Phenyl-2-ethanol	HMDB
2-Phenethanol	HMDB
2-Phenethyl alcohol	HMDB
2-PhenyIethanol	HMDB
2-Phenylethyl alcohol	HMDB
b-Hydroxyethylbenzene	HMDB
Benzeneethanol, 9ci	HMDB
Benzenethanol	HMDB
Benzyl carbinol	HMDB, MeSH
Benzyl ethyl alcohol	HMDB
Benzyl-methanol	HMDB
Benzylcarbinol	HMDB
beta -Hydroxyethylbenzene	HMDB
FEMA 2858	HMDB
Hydroxyethylbenzene	HMDB
Phenethanol	HMDB
Phenethyl alcohol, 8ci, ban	HMDB
Phenyl ethyl alcohol	HMDB
Phenyl-ethanol	HMDB
Phenylethanol	HMDB, MeSH
Phenylethyl alcohol, usan	HMDB
Alcohol, phenylethyl	MeSH, HMDB
Alcohol, phenethyl	MeSH, HMDB
beta Phenylethanol	MeSH, HMDB
2 Phenylethanol	MeSH, HMDB
Carbinol, benzyl	MeSH, HMDB

Chemical Formula

C₈H₁₀O

Average Molecular Weight

122.1644

Monoisotopic Molecular Weight

122.073164942

IUPAC Name

2-phenylethan-1-ol

Traditional Name

phenylethanol

CAS Registry Number

60-12-8

SMILES

OCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2

InChI Key

WRMNZCZEMHIOCP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

primary alcohol (CHEBI:49000 )
benzenes (CHEBI:49000 )
a small molecule (CPD-7035 )

Ontology

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-25.8 °C	Not Available
Boiling Point	219.00 to 221.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	22.2 mg/mL at 25 °C	Not Available
LogP	1.36	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	121.207	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000756

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.3 g/L	ALOGPS
logP	1.51	ALOGPS
logP	1.49	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	15.88	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.63 m³·mol⁻¹	ChemAxon
Polarizability	13.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	123.449	31661259
DarkChem	[M-H]-	120.677	31661259
DeepCCS	[M+H]+	124.888	30932474
DeepCCS	[M-H]-	122.019	30932474
DeepCCS	[M-2H]-	158.71	30932474
DeepCCS	[M+Na]+	133.549	30932474
AllCCS	[M+H]+	125.4	32859911
AllCCS	[M+H-H2O]+	120.6	32859911
AllCCS	[M+NH4]+	129.9	32859911
AllCCS	[M+Na]+	131.2	32859911
AllCCS	[M-H]-	125.3	32859911
AllCCS	[M+Na-2H]-	127.4	32859911
AllCCS	[M+HCOO]-	129.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.14 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9536 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.2 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1512.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	389.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	234.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	173.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	397.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	433.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	103.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	942.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	379.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1035.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	274.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	384.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	274.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	53.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Phenylethanol	OCCC1=CC=CC=C1	1871.2	Standard polar	33892256
2-Phenylethanol	OCCC1=CC=CC=C1	1090.0	Standard non polar	33892256
2-Phenylethanol	OCCC1=CC=CC=C1	1099.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Phenylethanol,1TMS,isomer #1	C[Si](C)(C)OCCC1=CC=CC=C1	1248.5	Semi standard non polar	33892256
2-Phenylethanol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC1=CC=CC=C1	1474.7	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Feces	Detected and Quantified	0-113972.101 nmol/g wet feces	Children (1-13 years old)	Not Specified	Normal	21970810	details
Feces	Detected and Quantified	27.286 (0-54.571) nmol/g wet feces	Children (1 - 13 years old)	Both	Normal	24130822	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details
Feces	Detected and Quantified	0-71406.509 nmol/g wet feces	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details
Feces	Detected and Quantified	27.286 (0-109.143) nmol/g wet feces	Children (1 - 13 years old)	Both	Autism	24130822	details
Feces	Detected and Quantified	27.286 (0-54.571) nmol/g wet feces	Children (1 - 13 years old)	Both	Developmental Disorder Not Otherwise Specified	24130822	details

Associated Disorders and Diseases

Disease References

Ulcerative colitis
Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Celiac disease
Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Autism
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]