AFCDB: 2-Phenylethanol (FDB012152)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:01 UTC

Update date

2019-11-26 03:06:16 UTC

Primary ID

FDB012152

Secondary Accession Numbers

FDB007516

Chemical Information

FooDB Name

2-Phenylethanol

Description

2-Phenylethanol, also known as phenethyl alcohol or 2-PEA, 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 plants 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 wine, black walnuts (Juglans nigra), and white wine and in a lower concentration in peppermints (Mentha X piperita), sweet basils (Ocimum basilicum), and bilberries (Vaccinium myrtillus). 2-Phenylethanol has also been detected, but not quantified in, several different foods, such as rowanberries (Sorbus aucuparia), elderberries (Sambucus), rocket salad (ssp.), napa cabbages (Brassica rapa var. pekinensis), and summer savories (Satureja hortensis). This could make 2-phenylethanol a potential biomarker for the consumption of these foods. 2-Phenylethanol, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, autism, and pervasive developmental disorder not otherwise specified; 2-phenylethanol has also been linked to the inborn metabolic disorder celiac disease. Based on a literature review a significant number of articles have been published on 2-Phenylethanol.

CAS Number

60-12-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted 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

Chemical Formula

C8H10O

IUPAC name

2-phenylethan-1-ol

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

Isomeric SMILES

OCCC1=CC=CC=C1

Average Molecular Weight

122.1644

Monoisotopic Molecular Weight

122.073164942

Classification

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Feces

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Pharmaceutical industry:

Pharmaceutical

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 78.65%; H 8.25%; O 13.10%	DFC
Melting Point	Mp -25.8°	DFC
Boiling Point	Bp10 99.5°	DFC
Experimental Water Solubility	22.2 mg/mL at 25 oC	VALVANI, SC et al. (1981)
Experimental logP	1.36	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d204 1.02	DFC
Refractive Index	n20D 1.5325	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9100000000-2e7748b750dd46a70f69	2015-03-01	View Spectrum
GC-MS	2-Phenylethan-1-ol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-850cab93c17d62d7ae48	Spectrum
GC-MS	2-Phenylethan-1-ol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-e67375f5607fb09ff117	Spectrum
GC-MS	2-Phenylethan-1-ol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-0ea4f78bf9f95dd3e378	Spectrum
GC-MS	2-Phenylethan-1-ol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-850cab93c17d62d7ae48	Spectrum
GC-MS	2-Phenylethan-1-ol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-e67375f5607fb09ff117	Spectrum
GC-MS	2-Phenylethan-1-ol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-0ea4f78bf9f95dd3e378	Spectrum
Predicted GC-MS	2-Phenylethan-1-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9200000000-12b145fa925fdbec3da0	Spectrum
Predicted GC-MS	2-Phenylethan-1-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0096-9300000000-143aa2e8abc3ff64d203	Spectrum
Predicted GC-MS	2-Phenylethan-1-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-0a4i-4900000000-01a904ef24c032004b01	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-0a4i-3900000000-ddf7f3974789f0591a55	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-0a4i-2900000000-f5f16d832b17b6c42111	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-0a6r-4900000000-798c6ceb60cef825b507	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-056r-9600000000-ab7ba9e5577110cb6606	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-004i-9400000000-f7bfe71e4407e811baac	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-004i-9200000000-fdd7461658bdfde8e166	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-004i-9100000000-3ee09fc79fd925fea86a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-004i-9000000000-8ca4cd35ef32af2c5ee6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-004i-9000000000-bc43025005b4fc0228ea	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-0fb9-9000000000-ebfd370a836a01c2e644	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-0ufr-9000000000-8eb5ed3477e91745eb8a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-0ufr-9000000000-08b0a4ab5c93b536ece3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0udi-9000000000-0016533929cda6a36167	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 45V, positive	splash10-0udi-9000000000-a64c19beae57204777f7	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0900000000-1568ff280886079d9591	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-e752bbf1c2351ee5aab5	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9600000000-a4927b67121bc2c9a1ed	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-3900000000-796d56c2e36ce04910a5	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-8900000000-3a23c6e7ffa45e886132	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f96-9300000000-5414e7814d2a11171734	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dl-7900000000-180ad2b2d5ea5abc75fc	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9300000000-dc57d0e64c13958600db	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-9000000000-4a2b1f87db1ff5c4e2a0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-7900000000-c5bfd86d969527f320b1	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB02192

HMDB ID

HMDB33944

CRC / DFC (Dictionary of Food Compounds) ID

HDT74-H:HDT74-H

EAFUS ID

2957

Dr. Duke ID

BIGG ID

Not Available

KNApSAcK ID

C00002663

HET ID

PEL

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

60-12-8

GoodScent ID

rw1010051

SuperScent ID

Not Available

Wikipedia ID

2-Phenylethanol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
motor depressant			DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
honey	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
spice	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
rose	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
lilac	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rose dried	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rose flower	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rose water	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

2-Phenylethanol (FDB012152)

Structure for FDB012152 (2-Phenylethanol)