AFCDB: 2-Isopropyl-5-methylphenol (FDB014795)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:28 UTC

Update date

2019-11-26 03:10:46 UTC

Primary ID

FDB014795

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Isopropyl-5-methylphenol

Description

Found in many essential oils. Especies found in the Labiatae. Rich sources are thyme oil, seed oil of Ptychotis ajowan and oils of horsemint (Monarda punctata) and Ocimum subspecies Flavouring ingredient A phenol obtained from thyme oil or other volatile oils. It is used as a stabilizer in pharmaceutic preparations. It has been used for its antiseptic, antibacterial, and antifungal actions, and was formerly used as a vermifuge. (Dorland, 28th ed) -- Pubchem; In a 1994 report released by five top cigarette companies, thymol is one of the 599 additives to cigarettes. Its use or purpose, however, is unknown, like most cigarette additives. -- Wikipedia; In a 1994 report released by five top cigarette companies, thymol was listed as one of 599 additives to cigarettes. It is said to be added to improve the flavor of cigarettes, but as mentioned above, it relaxes the trachea.; Thymol (also known as 2-isopropyl-5-methylphenol), (IPMP) is a monoterpene phenol derivative of cymene, C10H14O, isomeric with carvacrol, found in oil of thyme, and extracted as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Thymol is only slightly soluble in water, but it is extremely soluble in alcohols and other organic solvents. It is also called "Isopropyl-m-cresol" and "hydroxy cymene".; Thymol is a monoterpene phenol derivative of cymene, C10H13OH, isomeric with carvacrol, found in oil of thyme, and extracted as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. It is also called "hydroxy cymene". (from Webster's 1913 dictionary) -- Wikipedia

CAS Number

89-83-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.64 g/L	ALOGPS
logP	3.16	ALOGPS
logP	3.43	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	10.59	ChemAxon
pKa (Strongest Basic)	-5.2	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	47.27 m³·mol⁻¹	ChemAxon
Polarizability	17.84 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

C10H14O

IUPAC name

5-methyl-2-(propan-2-yl)phenol

InChI Identifier

InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h4-7,11H,1-3H3

InChI Key

MGSRCZKZVOBKFT-UHFFFAOYSA-N

Isomeric SMILES

CC(C)C1=C(O)C=C(C)C=C1

Average Molecular Weight

150.221

Monoisotopic Molecular Weight

150.104465071

Classification

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Cumene
Phenylpropane
M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Benzenoid
Monocyclic benzene moiety
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:27607 )
monoterpenoid (CHEBI:27607 )
Menthane monoterpenoids (C09908 )
Cyclic monoterpenes (C09908 )
Menthane monoterpenoids (LMPR0102090029 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 79.96%; H 9.39%; O 10.65%	DFC
Melting Point	Mp 51.5°	DFC
Boiling Point	Bp10 115°	DFC
Experimental Water Solubility	0.9 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	3.30	HANSCH,C ET AL. (1995)
Experimental pKa	pKa1 10.62 (20°)	DFC
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)	splash10-000i-4900000000-73edaa628c1f5f2e1bd9	2015-03-01	View Spectrum
GC-MS	Thymunic acid, non-derivatized, GC-MS Spectrum	splash10-000i-0900000000-333dc57384e65e3b4cfa	Spectrum
GC-MS	Thymunic acid, non-derivatized, GC-MS Spectrum	splash10-000i-1900000000-3679938a5ea114a30e48	Spectrum
GC-MS	Thymunic acid, non-derivatized, GC-MS Spectrum	splash10-000i-3900000000-8ce5865e48dad7250d5e	Spectrum
GC-MS	Thymunic acid, non-derivatized, GC-MS Spectrum	splash10-0udi-0109030000-5562c203cb318f30321b	Spectrum
GC-MS	Thymunic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-2492200000-85342d698be72263a95f	Spectrum
GC-MS	Thymunic acid, non-derivatized, GC-MS Spectrum	splash10-000i-0900000000-333dc57384e65e3b4cfa	Spectrum
GC-MS	Thymunic acid, non-derivatized, GC-MS Spectrum	splash10-000i-1900000000-3679938a5ea114a30e48	Spectrum
GC-MS	Thymunic acid, non-derivatized, GC-MS Spectrum	splash10-000i-3900000000-8ce5865e48dad7250d5e	Spectrum
GC-MS	Thymunic acid, non-derivatized, GC-MS Spectrum	splash10-0udi-0109030000-5562c203cb318f30321b	Spectrum
GC-MS	Thymunic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-2492200000-85342d698be72263a95f	Spectrum
Predicted GC-MS	Thymunic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f79-3900000000-e309fdc1ab0cd926b420	Spectrum
Predicted GC-MS	Thymunic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-9880000000-3a69bebdbca0f95e862a	Spectrum
Predicted GC-MS	Thymunic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Thymunic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-01p9-9700000000-e1a28495617d7b014e5c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9300000000-baeee6cdcafaadeebdec	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-015c-9100000000-e1efa41eaf818832448a	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positive	splash10-000i-0900000000-333dc57384e65e3b4cfa	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-000i-1900000000-3679938a5ea114a30e48	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-000i-3900000000-f72f603d97f0f7081b8d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-QFT 10V, negative	splash10-0002-0900000000-d3ae016121d86e17ddb4	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-QFT 13V, negative	splash10-0002-1900000000-3e340243a54a9e3f0da4	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-QFT 19V, negative	splash10-00dm-8900000000-82e846f2a3546e27414c	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-0002-0900000000-844f0c545c66f6c63993	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, negative	splash10-0a4i-0900000000-d30a5d305446b3540d85	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-2900000000-4e6c9c70215576f53b60	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-001i-2900000000-eeb06bc7587fcef0ba86	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-a8236f8b0194b3d08844	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-be4566e335ee9b00c724	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-fde7d3d2a42203ba2b95	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-92d1da1fba9df31389ed	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-32e3f430e6dfc819272b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-2900000000-19305d290c7303afc3f5	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pw9-7900000000-b0fcecf9ea71d3528408	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-1b21dedfdc78e416ea8f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-43b3e1a99ba193849bf4	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0532-3900000000-a152936b0bcf0d320092	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052f-9800000000-947167dd66d5b6947416	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9600000000-df6822dada158a51482c	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Phenol-Explorer ID

DrugBank ID

HMDB ID

CRC / DFC (Dictionary of Food Compounds) ID

JVX23-D:JVX23-D

EAFUS ID

3678

Dr. Duke ID

THYMOL

BIGG ID

Not Available

KNApSAcK ID

C00000155

HET ID

IPB

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1019911

SuperScent ID

Not Available

Wikipedia ID

Thymol

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
acaricide	22153	A substance used to destroy pests of the subclass Acari (mites and ticks).	DUKE
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
ancylostomicide			DUKE
anesthetic			DUKE
ankylostomacide	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti helmintic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti acne	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti aggregant			DUKE
anti Alzheimeran	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti arthritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti atherosclerotic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti bronchitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cariogenic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cholinesterase	37733	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).	DUKE
anti halitosic			DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti lepric	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti melanomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti neuritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti periodontic			DUKE
anti plaque			DUKE
anti radicular			DUKE
anti rheumatic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti salmonella	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
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti streptococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti trichinosic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti tussive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
ataxigenic			DUKE
candidicide			DUKE
carminative			DUKE
counterirritant			DUKE
culicide			DUKE
cyclooxygenase inhibitor	35544	A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.	DUKE
dentifrice			DUKE
deodorant			DUKE
dermatitigenic			DUKE
enterorelaxant			DUKE
enterotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
expectorant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
gastroirritant			DUKE
Gram(+)icide	33282	A substance that kills or slows the growth of bacteria.	DUKE
Gram(-)icide	33282	A substance that kills or slows the growth of bacteria.	DUKE
insecticide	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
insectifuge	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
irritant			DUKE
larvicide			DUKE
molluscicide	33904	A substance used to destroy pests of the phylum Mollusca.	DUKE
myorelaxant			DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	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
sprout inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
tracheorelaxant			DUKE
trichomonicide			DUKE
urinary antiseptic			DUKE
varroacide			DUKE
vermicide			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
herbal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
thyme	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
phenolic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medicinal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphor	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).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

2-Isopropyl-5-methylphenol (FDB014795)

Structure for FDB014795 (2-Isopropyl-5-methylphenol)