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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:23 UTC

Update Date

2023-02-21 17:21:00 UTC

HMDB ID

HMDB0031616

Secondary Accession Numbers

HMDB31616

Metabolite Identification

Common Name

4-Phenyl-3-buten-2-ol

Description

4-Phenyl-3-buten-2-ol belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety. 4-Phenyl-3-buten-2-ol is a sweet, balsam, and floral tasting compound. Based on a literature review a small amount of articles have been published on 4-Phenyl-3-buten-2-ol.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Methylcinnamyl alcohol	HMDB
FEMA 2880	HMDB
Methylstyrylcarbinol	HMDB

Chemical Formula

C₁₀H₁₂O

Average Molecular Weight

148.2017

Monoisotopic Molecular Weight

148.088815006

IUPAC Name

(3Z)-4-phenylbut-3-en-2-ol

Traditional Name

(3Z)-4-phenylbut-3-en-2-ol

CAS Registry Number

17488-65-2

SMILES

CC(O)\C=C/C1=CC=CC=C1

InChI Identifier

InChI=1S/C10H12O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-9,11H,1H3/b8-7-

InChI Key

ZIJWGEHOVHJHKB-FPLPWBNLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamyl alcohols

Sub Class

Not Available

Direct Parent

Cinnamyl alcohols

Alternative Parents

Substituents

Cinnamyl alcohol
Styrene
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB31616)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	140.00 °C. @ 12.00 mm Hg	The Good Scents Company Information System
Water Solubility	2935 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.043 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.49 g/L	ALOGPS
logP	2.42	ALOGPS
logP	2.23	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	15.29	ChemAxon
pKa (Strongest Basic)	-2.7	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	47.61 m³·mol⁻¹	ChemAxon
Polarizability	17.1 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]+	136.936	31661259
DarkChem	[M-H]-	132.324	31661259
DeepCCS	[M+H]+	132.57	30932474
DeepCCS	[M-H]-	129.286	30932474
DeepCCS	[M-2H]-	166.254	30932474
DeepCCS	[M+Na]+	141.79	30932474
AllCCS	[M+H]+	131.5	32859911
AllCCS	[M+H-H2O]+	126.8	32859911
AllCCS	[M+NH4]+	135.8	32859911
AllCCS	[M+Na]+	137.0	32859911
AllCCS	[M-H]-	132.7	32859911
AllCCS	[M+Na-2H]-	134.0	32859911
AllCCS	[M+HCOO]-	135.5	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.	5.67 minutes	32390414
Predicted by Siyang on May 30, 2022	11.722 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.62 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2049.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	383.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	142.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	222.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	172.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	433.2 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	472.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1082.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	415.0 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	987.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	356.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	359.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	267.8 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	10.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Phenyl-3-buten-2-ol	CC(O)\C=C/C1=CC=CC=C1	2198.7	Standard polar	33892256
4-Phenyl-3-buten-2-ol	CC(O)\C=C/C1=CC=CC=C1	1264.8	Standard non polar	33892256
4-Phenyl-3-buten-2-ol	CC(O)\C=C/C1=CC=CC=C1	1274.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Phenyl-3-buten-2-ol,1TMS,isomer #1	CC(/C=C\C1=CC=CC=C1)O[Si](C)(C)C	1400.5	Semi standard non polar	33892256
4-Phenyl-3-buten-2-ol,1TBDMS,isomer #1	CC(/C=C\C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	1665.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Phenyl-3-buten-2-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ue9-5900000000-15afd09ca2ee6acb4067	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Phenyl-3-buten-2-ol GC-MS (1 TMS) - 70eV, Positive	splash10-05j3-9420000000-7186034ff8ca098856d6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Phenyl-3-buten-2-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-3-buten-2-ol 10V, Positive-QTOF	splash10-001i-0900000000-d3f3dba652ef12061fb0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-3-buten-2-ol 20V, Positive-QTOF	splash10-001i-3900000000-18c1a52edd51b8325a9e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-3-buten-2-ol 40V, Positive-QTOF	splash10-0f6x-9300000000-56b3f0744fefe8c8993a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-3-buten-2-ol 10V, Negative-QTOF	splash10-0002-0900000000-a5afbe7c5a5ffecb05d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-3-buten-2-ol 20V, Negative-QTOF	splash10-002b-0900000000-4ec3a2bf1ffb243f97bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-3-buten-2-ol 40V, Negative-QTOF	splash10-0kei-7900000000-6fed1665e34158512f26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-3-buten-2-ol 10V, Negative-QTOF	splash10-0002-0900000000-8472d810ced16088d749	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-3-buten-2-ol 20V, Negative-QTOF	splash10-0udj-1900000000-606b9d7918b7377126fb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-3-buten-2-ol 40V, Negative-QTOF	splash10-0h00-9500000000-a2dd9233c8bfd36d9f2d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-3-buten-2-ol 10V, Positive-QTOF	splash10-001i-1900000000-5070e17993f9244bfeb3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-3-buten-2-ol 20V, Positive-QTOF	splash10-0uec-4900000000-23c485e128189c510bf9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-3-buten-2-ol 40V, Positive-QTOF	splash10-0ftf-9600000000-9bb3703dad1317b09b2d	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008253

KNApSAcK ID

Not Available

Chemspider ID

9643981

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11469151

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1033841

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Phenyl-3-buten-2-ol (HMDB0031616)

MOL for HMDB0031616 (4-Phenyl-3-buten-2-ol)

3D MOL for HMDB0031616 (4-Phenyl-3-buten-2-ol)

3D SDF for HMDB0031616 (4-Phenyl-3-buten-2-ol)

3D-SDF for HMDB0031616 (4-Phenyl-3-buten-2-ol)

PDB for HMDB0031616 (4-Phenyl-3-buten-2-ol)

3D PDB for HMDB0031616 (4-Phenyl-3-buten-2-ol)

SMILES for HMDB0031616 (4-Phenyl-3-buten-2-ol)

INCHI for HMDB0031616 (4-Phenyl-3-buten-2-ol)

Structure for HMDB0031616 (4-Phenyl-3-buten-2-ol)

3D Structure for HMDB0031616 (4-Phenyl-3-buten-2-ol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra