naphthalene (YMDB01393)

Identification

YMDB ID

YMDB01393

Name

naphthalene

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Naphthalene is an organic compound with formula C10H8. It is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is best known as the main ingredient of traditional mothballs. Trace amounts of naphthalene are produced by magnolias and specific types of deer, as well as the Formosan subterranean termite, possibly produced by the termite as a repellant against "ants, poisonous fungi and nematode worms." Some strains of the endophytic fungus Muscodor albus produce naphthalene among a range of volatile organic compounds, while Muscodor vitigenus produces naphthalene almost exclusively. [Wikipedia]

Structure

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

Synonyms

Albocarbon
Camphor tar
Dezodorator
Mighty rd1
Moth balls
Moth flakes
naftaleno
naftalina
naphtalene
naphtaline
Naphthalen
Naphthalene
Naphthalin
Naphthaline
Naphthene
Tar camphor
White tar
Mothballs
Naftalen
Tolboxane

CAS number

91-20-3

Weight

Average: 128.1705
Monoisotopic: 128.062600256

InChI Key

UFWIBTONFRDIAS-UHFFFAOYSA-N

InChI

InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H

IUPAC Name

naphthalene

Traditional IUPAC Name

naphthalene

Chemical Formula

C₁₀H₈

SMILES

[H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C([H])=C1[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Aromatic hydrocarbon
Polycyclic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthalenes (CHEBI:16482 )
ortho-fused bicyclic arene (CHEBI:16482 )
Fumigants (C00829 )
an aromatic compound (NAPHTHALENE )

Physical Properties

State

Solid

Charge

Melting point

80.2 °C

Experimental Properties

Property	Value	Reference
Water Solubility	0.031 mg/mL at 25 oC [PEARLMAN,RS et al. (1984)]	PhysProp
LogP	3.30 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.066 g/L	ALOGPS
logP	3.33	ALOGPS
logP	2.96	ChemAxon
logS	-3.3	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.51 m³·mol⁻¹	ChemAxon
Polarizability	14.56 Å³	ChemAxon
Number of Rings	2	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
Dry	FDB000954
Pungent	FDB000954
Tar	FDB000954
Tarry	FDB000954

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 - EI-B (Non-derivatized)	splash10-004i-4900000000-28274068093bf0319e30	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-10810744223497787156	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0900000000-f640b15d5ebd285008e9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-2900000000-837afe39d2806871be73	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-5900000000-262e4b8e72f3d3fa0593	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-3900000000-0e32d0a2d4bb6373bea3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-34ade0e20ab7aa4d4e7f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-c780f74ca6838fbab7d8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-4900000000-b2e474b4d7508faeddc3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-7900000000-43781a61560faeff786d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-0900000000-7a87251d344c519a4335	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-004i-0900000000-0532459557fd0c543587	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-1900000000-5a22b095f0a190f1b978	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-28274068093bf0319e30	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-10810744223497787156	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0900000000-f640b15d5ebd285008e9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-2900000000-837afe39d2806871be73	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-5900000000-262e4b8e72f3d3fa0593	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-3900000000-0e32d0a2d4bb6373bea3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-34ade0e20ab7aa4d4e7f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-c780f74ca6838fbab7d8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-4900000000-b2e474b4d7508faeddc3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-7900000000-43781a61560faeff786d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-0900000000-7a87251d344c519a4335	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-1900000000-35bf92cf7a210b27759b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-9058dd9b60d558e52773	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-9058dd9b60d558e52773	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1900000000-91e4df79f1f59e0c0465	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8575b97da509996b8151	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-8575b97da509996b8151	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-ff7fd755c09159064a33	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-71e8922109bea9aa624a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-6900000000-6558deffdb05b27a632e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-3900000000-f1f49df790d7f67edbc0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-ec6816397577a7beb93f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-ec6816397577a7beb93f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-ec6816397577a7beb93f	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-004i-2900000000-1f03568d4331683921b4	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C 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

References

References:

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:

Not Available

External Links:

Resource	Link
CHEBI ID	16482
HMDB ID	HMDB0029751
Pubchem Compound ID	931
Kegg ID	C00829
ChemSpider ID	906
FOODB ID	FDB000954
Wikipedia	naphthalene
BioCyc ID	Not Available

Structure for #<Compound:0xad0ab09c>