Showing Compound Phloroglucinol (FDB013879)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:57 UTC

Update date

2020-09-17 15:39:53 UTC

Primary ID

FDB013879

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Phloroglucinol

Description

1,3,5-Trihydroxybenzene, also known as 1,3,5-benzenetriol or benzene-1,3,5-triol, belongs to the class of organic compounds known as phloroglucinols and derivatives. Phloroglucinols and derivatives are compounds containing a phloroglucinol (benzene-1,3,5-triol) moiety, which consists of a benzene ring bearing one hydroxyl group at positions 1,3, and 5. It is an organic compound that is used in the synthesis of pharmaceuticals and explosives. This molecule exists in two forms, or tautomers, 1,3,5-trihydroxybenzene, which has phenol-like, and 1,3,5-cyclohexanetrione (phloroglucin), which has ketone-like character. 1,3,5-Trihydroxybenzene has been found to be a metabolite in Pseudomonas (PMID: 15826166). 1,3,5-Trihydroxybenzene is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1,3,5-Trihydroxybenzene is found, on average, in the highest concentration within garden onions. 1,3,5-Trihydroxybenzene has also been detected, but not quantified in, several different foods, such as carobs, highbush blueberries, soft-necked garlics, tarragons, and tea. This could make 1,3,5-trihydroxybenzene a potential biomarker for the consumption of these foods. These two tautomers are in equilibrium. Phloroglucinol is a useful intermediate because it is polyfunctional. Phloroglucinol is a benzenetriol.

CAS Number

108-73-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,3,5-Benzenetriol	ChEBI
Benzene-1,3,5-triol	ChEBI
S-Trihydroxybenzene	ChEBI
Dilospan S	Kegg
1,3,5-Trihydroxybenzene	ChEBI
1,3, 5-Trihydroxybenzene	HMDB
1,3,5-Benzenetriol (acd/name 4.0)	HMDB
1,3,5-Trihydroxy-benzene	HMDB
1,3,5-Trihydroxycyclohexatriene	HMDB
1,3,5-Triol	HMDB
3,5-Dihydroxyphenol	HMDB
5-Benzenetriol	HMDB
5-Hydroxyresorcinol	HMDB
5-Oxyresorcinol	HMDB
5-Oxyresorcinolphloroglucin	HMDB
Benzene, trihydroxy	HMDB
Benzene-S-triol	HMDB
Floroglucin	HMDB
Floroglucinol	HMDB
Phloroglucin	HMDB
Phloroglucine	HMDB
Phloroglucinol (1,3,5-benzenetriol)	HMDB
Spasfon-lyoc	HMDB, MeSH
Sym-trihydroxybenzene	HMDB
Spassirex	MeSH
Phloroglucinol	HMDB
Spasfon-Lyoc	db_source

Predicted Properties

Property	Value	Source
Water Solubility	35.8 g/L	ALOGPS
logP	0.25	ALOGPS
logP	1.06	ChemAxon
logS	-0.55	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	32 m³·mol⁻¹	ChemAxon
Polarizability	11.69 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H6O3

IUPAC name

benzene-1,3,5-triol

InChI Identifier

InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H

InChI Key

QCDYQQDYXPDABM-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC(O)=CC(O)=C1

Average Molecular Weight

126.11

Monoisotopic Molecular Weight

126.031694058

Classification

Description

Belongs to the class of organic compounds known as phloroglucinols and derivatives. Phloroglucinols and derivatives are compounds containing a phloroglucinol (benzene-1,3,5-triol) moiety, which consists of a benzene ring bearing one hydroxyl group at positions 1,3, and 5.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

Benzenetriols and derivatives

Direct Parent

Phloroglucinols and derivatives

Alternative Parents

Substituents

Phloroglucinol derivative
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzenetriol (CHEBI:16204 )
a small molecule (CPD-16 )

Ontology

Disposition

Biological location:

Biofluid and excreta:

Feces

Source:

Endogenous

Biological:

Microbe:

Pseudomonas:

Pseudomonas fluorescens

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 57.14%; H 4.80%; O 38.06%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
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
GC-MS	Phloroglucinol, non-derivatized, GC-MS Spectrum	splash10-0037-1925000000-c724191b9103115057ca	Spectrum
GC-MS	Phloroglucinol, non-derivatized, GC-MS Spectrum	splash10-0037-1925000000-c724191b9103115057ca	Spectrum
Predicted GC-MS	Phloroglucinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-1900000000-dd0ed35d23318896d1b9	Spectrum
Predicted GC-MS	Phloroglucinol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9266000000-2317d43ce1d2bdb60083	Spectrum
Predicted GC-MS	Phloroglucinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phloroglucinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9000000000-104015e2f367513be83d	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-000o-9000000000-66ca2cf660ad4426c021	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-1900000000-d25737e313306ff2b48d	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-004i-1900000000-6a0b9a2f7d646e89cea4	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-004i-3900000000-d102992a3cf4a244a8c6	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-004i-7900000000-e4022d17507410f9dea6	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-0a6r-9500000000-efa09c9675e92917dc71	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-0a4i-9200000000-b8189deed5b441103a17	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-0a4i-9100000000-91c096b5c6bca93fb201	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-0a4i-9000000000-2dfdf462ad4af57dd4ee	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-0a4i-9000000000-0e5ee4e7603fdee5aa91	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, negative	splash10-0a4i-9000000000-ee965d165837c624e0a4	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-0a4i-9000000000-42a5aadbd8a2700fcb8a	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, negative	splash10-0a4i-9000000000-ced455fb5a135cb19c2e	Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 8V, negative	splash10-001i-9000000000-23bf2d29b2666f3f65fa	Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-004i-0900000000-4e75317d3710eb5b0c50	Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-004i-0900000000-944db6cc318783777622	Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-004i-0900000000-c9f3189fb88bc03828f1	Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-004i-0900000000-11900ad61e01b6d4449b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-85c95c94bd781f89f712	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-75dcf760031bb09416a1	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2900000000-8f7164ec36db279bbbbf	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-09436c8cdb204e5cecb4	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-46ba64f6b6c946b31aae	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-6900000000-776dffab62c69a4b4b02	Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

658

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

JJJ54-P:JJJ54-P

EAFUS ID

Not Available

Dr. Duke ID

1,3,5-TRIHYDROXY-BENZENE|PHLOROGLUCINOL

BIGG ID

Not Available

KNApSAcK ID

C00002665

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

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
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
antitumor promoter	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
decalcifier			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
goitrogenic			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
prostaglandin synthesis inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE