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Phloroglucinol (FDB013879)

Record Information
Version1.0
Creation date2010-04-08 22:10:57 UTC
Update date2020-09-17 15:39:53 UTC
Primary IDFDB013879
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhloroglucinol
Description1,3,5-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 Number108-73-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility35.8 g/LALOGPS
logP0.25ALOGPS
logP1.06ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)9.13ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32 m³·mol⁻¹ChemAxon
Polarizability11.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H6O3
IUPAC namebenzene-1,3,5-triol
InChI IdentifierInChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
InChI KeyQCDYQQDYXPDABM-UHFFFAOYSA-N
Isomeric SMILESOC1=CC(O)=CC(O)=C1
Average Molecular Weight126.11
Monoisotopic Molecular Weight126.031694058
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenetriols and derivatives
Direct ParentPhloroglucinols 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 57.14%; H 4.80%; O 38.06%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPhloroglucinol, non-derivatized, GC-MS Spectrumsplash10-0037-1925000000-c724191b9103115057caSpectrum
GC-MSPhloroglucinol, non-derivatized, GC-MS Spectrumsplash10-0037-1925000000-c724191b9103115057caSpectrum
Predicted GC-MSPhloroglucinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-1900000000-dd0ed35d23318896d1b9Spectrum
Predicted GC-MSPhloroglucinol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9266000000-2317d43ce1d2bdb60083Spectrum
Predicted GC-MSPhloroglucinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhloroglucinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-104015e2f367513be83d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-000o-9000000000-66ca2cf660ad4426c0212020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-1900000000-d25737e313306ff2b48d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-1900000000-6a0b9a2f7d646e89cea42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-3900000000-d102992a3cf4a244a8c62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-004i-7900000000-e4022d17507410f9dea62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0a6r-9500000000-efa09c9675e92917dc712020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0a4i-9200000000-b8189deed5b441103a172020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-9100000000-91c096b5c6bca93fb2012020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-9000000000-2dfdf462ad4af57dd4ee2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0a4i-9000000000-0e5ee4e7603fdee5aa912020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-0a4i-9000000000-ee965d165837c624e0a42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0a4i-9000000000-42a5aadbd8a2700fcb8a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-0a4i-9000000000-ced455fb5a135cb19c2e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-001i-9000000000-23bf2d29b2666f3f65fa2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-004i-0900000000-4e75317d3710eb5b0c502020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-004i-0900000000-944db6cc3187837776222020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-004i-0900000000-c9f3189fb88bc03828f12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-004i-0900000000-11900ad61e01b6d4449b2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-85c95c94bd781f89f7122016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-75dcf760031bb09416a12016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-8f7164ec36db279bbbbf2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-09436c8cdb204e5cecb42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-46ba64f6b6c946b31aae2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-6900000000-776dffab62c69a4b4b022016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID658
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJJJ54-P:JJJ54-P
EAFUS IDNot Available
Dr. Duke ID1,3,5-TRIHYDROXY-BENZENE|PHLOROGLUCINOL
BIGG IDNot Available
KNApSAcK IDC00002665
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
decalcifierDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
goitrogenicDUKE
pesticide25944 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 inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.