benzyl alcohol (YMDB01426)

Identification

YMDB ID

YMDB01426

Name

benzyl alcohol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Benzyl alcohol, also known as alpha-toluenol or aromatic alcohol, belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure. Benzyl alcohol exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Benzyl alcohol.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

.alpha.-hydroxytoluene
.alpha.-toluenol
(hydroxymethyl)benzene
a-Hydroxytoluene
a-Toluenol
alcoholum benzylicum
Alcool benzylique
alpha-hydroxytoluene
Alpha-toluenol
Aromatic primary alcohol
Bentalol
Benzal alcohol
Benzenecarbinol
Benzenemethanol
benzenmethanol
Benzoyl alcohol
Benzyl alcohol
Benzyl alkohol
Benzyl-alcohol
BenzylAlcohol
Benzylalkohol
Benzylic alcohol
Benzylicum
Enzylalcohol
hydroxymethylbenzene
Hydroxytoluene
MBN
Methanol benzene
Methanol, phenyl-
Phenolcarbinol
Phenylcarbinol
Phenylcarbinolum
phenylmethanol
Phenylmethyl alcohol
Aromatic alcohol
Ulesfia
Α-hydroxytoluene
Α-toluenol
Alcohol, benzyl
Caswell no. 081F
Euxyl K 100
Itch-X
Sunmorl BK 20
TB 13g

CAS number

100-51-6

Weight

Average: 108.1378
Monoisotopic: 108.057514878

InChI Key

WVDDGKGOMKODPV-UHFFFAOYSA-N

InChI

InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2

IUPAC Name

phenylmethanol

Traditional IUPAC Name

benzyl alcohol

Chemical Formula

C₇H₈O

SMILES

OCC1=CC=CC=C1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyl alcohols

Direct Parent

Benzyl alcohols

Alternative Parents

Substituents

Benzyl alcohol
Organic oxygen compound
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzyl alcohols (CHEBI:17987 )
an aromatic compound (BENZYL-ALCOHOL )

Physical Properties

State

Liquid

Charge

Melting point

-15.2 °C

Experimental Properties

Property	Value	Reference
Water Solubility	42.9 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	1.10 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	26.8 g/L	ALOGPS
logP	1.07	ALOGPS
logP	1.21	ChemAxon
logS	-0.61	ALOGPS
pKa (Strongest Acidic)	15.02	ChemAxon
pKa (Strongest Basic)	-2.8	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	1	ChemAxon
Refractivity	32.87 m³·mol⁻¹	ChemAxon
Polarizability	11.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular

Organoleptic Properties

Flavour/Odour	Source
Balsamic	FDB008745
Berry	FDB008745
Cherry	FDB008745
Floral	FDB008745
Flower	FDB008745
Grapefruit	FDB008745
Phenolic	FDB008745
Rose	FDB008745
Sweet	FDB008745
Walnut	FDB008745

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00ko-6900000000-a9d668ecd37a1579a6fe	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-056r-9400000000-77cec715500da9c57a84	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-056r-9400000000-8dc38068387df3fa06aa	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-056r-9300000000-fb124b56257906cce9f1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-056r-9400000000-7a77e67486ae3b2dd855	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-056r-9400000000-dd0878988e7c2d9a5431	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00ko-6900000000-a9d668ecd37a1579a6fe	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-8900000000-c256b0b7a0755f08ac64	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-9200000000-a9f7c0f39c81d478c0d4	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9300000000-e1cfa5e819f61adf9df2	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0a4i-9500000000-2a82c3dd7c6871f61c34	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0006-9000000000-ad1762d5292c30b29bbd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0006-9000000000-3c8d4c630cf42e3bfd3f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-056r-9400000000-c4dcb2148958f946cd01	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-056r-9400000000-e17e577dbe4546313a91	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-056r-9300000000-fb124b56257906cce9f1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-056r-9400000000-47b3605316c57e02b84f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-056r-9400000000-dd0878988e7c2d9a5431	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-3900000000-4d1bf15f6cf8f65bf0a6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-1900000000-866ce230a3fc1ead8353	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-3a71c23796a048eb999c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-40737e7bdf548d714249	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-9100000000-23e82914cfa9372ecafc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1900000000-17f95f5a398b5850abb2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6r-7900000000-733d283e0916e755a736	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-d0c6e5fc39516ee594b4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-d0618c117a092a2f7241	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-b65b57d5b2389beaf5f2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-a2b78129c0731eee69f4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9200000000-72dc044d901c3dfcec51	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-fc58e0949de9ca4842ff	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-fc58e0949de9ca4842ff	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-056r-9400000000-a8f1fd78fa3f8781f296	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). "Yeast influence on volatile composition of wines." J Agric Food Chem 47:1139-1144.10552428
Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225
Patel, S., Shibamoto, T. (2002). "Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine." J Agric Food Chem 50:5649-5653.12236692

Synthesis Reference:

Xu, Hua-Long; Huang, Jing-Jing; Yang, Xin-Yan; Du, Jun-Ming; Shen, Jiang; Shen, Wei. Consecutive hydrogenation of methyl benzoate to non-chloride benzyl alcohol over K-MnO/g-Al2O3 and Cu/SiO2 catalysts. Huaxue Xuebao (2006), 64(16), 1615-1621.

External Links:

Resource	Link
CHEBI ID	17987
HMDB ID	HMDB03119
Pubchem Compound ID	244
Kegg ID	C00556
ChemSpider ID	13860335
FOODB ID	FDB008745
Wikipedia	benzyl_alcohol
BioCyc ID	34-DIMETHYLBENZYL-ALCOHOL

Structure for #<Compound:0x9d9a36b4>