AFCDB: Naphthalene (FDB000954)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:46 UTC

Update date

2020-02-24 19:10:17 UTC

Primary ID

FDB000954

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Naphthalene

Description

Found in many essential oils 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. Trace amounts of naphthalene are produced by magnolias and specific types of deer, as well as the Formosan subterranean termite. Some strains of the endophytic fungus Muscodor albus produce naphthalene among a range of volatile organic compounds, while Muscodor vitigenus produces naphthalene almost exclusively .

CAS Number

91-20-3

Structure

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

Synonyms

Synonym	Source
Not Available	Not Available

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H8

IUPAC name

naphthalene

InChI Identifier

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

InChI Key

UFWIBTONFRDIAS-UHFFFAOYSA-N

Isomeric SMILES

C1=CC2=CC=CC=C2C=C1

Average Molecular Weight

128.1705

Monoisotopic Molecular Weight

128.062600256

Classification

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 )

Ontology

Physiological effect

Health effect:

Health condition:

Blood and lymphatic system disorders:

Anemia

Psychiatric disorders:

Confusion

Gastrointestinal disorders:

General disorders and administration site conditions:

Fatigue

Observation:

Jaundice

Disposition

Route of exposure:

Parenteral:

Inhalation

Enteral:

Ingestion

Source:

Environmental:

Tobacco smoke

Biological:

Plant:

Poaceae

Biological location:

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Asthma

Role

Indirect biological role:

Carcinogen

Environmental role:

Industrial application:

Food and nutrition

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 93.71%; H 6.29%	DFC
Melting Point	Mp 80.3°	DFC
Boiling Point	Bp 218°	DFC
Experimental Water Solubility	0.031 mg/mL at 25 oC	PEARLMAN,RS et al. (1984)
Experimental logP	3.30	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	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-004i-2900000000-1f03568d4331683921b4	2014-09-20	View Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-28274068093bf0319e30	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-10810744223497787156	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-0900000000-f640b15d5ebd285008e9	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-2900000000-837afe39d2806871be73	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-5900000000-262e4b8e72f3d3fa0593	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-3900000000-0e32d0a2d4bb6373bea3	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-34ade0e20ab7aa4d4e7f	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-c780f74ca6838fbab7d8	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-000i-4900000000-b2e474b4d7508faeddc3	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-7900000000-43781a61560faeff786d	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-000i-0900000000-7a87251d344c519a4335	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-0900000000-0532459557fd0c543587	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-1900000000-5a22b095f0a190f1b978	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-28274068093bf0319e30	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-10810744223497787156	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-0900000000-f640b15d5ebd285008e9	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-2900000000-837afe39d2806871be73	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-5900000000-262e4b8e72f3d3fa0593	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-3900000000-0e32d0a2d4bb6373bea3	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-34ade0e20ab7aa4d4e7f	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-c780f74ca6838fbab7d8	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-000i-4900000000-b2e474b4d7508faeddc3	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-7900000000-43781a61560faeff786d	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-000i-0900000000-7a87251d344c519a4335	Spectrum
Predicted GC-MS	Naphthalene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-1900000000-35bf92cf7a210b27759b	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-9058dd9b60d558e52773	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-9058dd9b60d558e52773	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1900000000-91e4df79f1f59e0c0465	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8575b97da509996b8151	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-8575b97da509996b8151	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-ff7fd755c09159064a33	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-71e8922109bea9aa624a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-6900000000-6558deffdb05b27a632e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-3900000000-f1f49df790d7f67edbc0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-ec6816397577a7beb93f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-ec6816397577a7beb93f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-ec6816397577a7beb93f	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16482

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB29751

CRC / DFC (Dictionary of Food Compounds) ID

BNK69-U:BNK69-U

EAFUS ID

Not Available

Dr. Duke ID

NAPHTHALINE|NAPHTHALENE

BIGG ID

Not Available

KNApSAcK ID

C00001259

HET ID

NPY

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

91-20-3

GoodScent ID

rw1268211

SuperScent ID

Not Available

Wikipedia ID

Naphthalene

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
cataractagenic			DUKE
carcinogenic	50903	A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
tar	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
pungent	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
dry	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tarry	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

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).

Naphthalene (FDB000954)

Structure for FDB000954 (Naphthalene)