2',4',6'-Trihydroxyacetophenone (HCID 68073)

Overview

2',4',6'-trihydroxyacetophenone is a benzenetriol that is acetophenone in which the hydrogens at positions 2, 4, and 6 on the phenyl group are replaced by hydroxy groups. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of acidic glycans and glycopeptides. It has a role as a MALDI matrix material and a plant metabolite. It is a benzenetriol, a methyl ketone and an aromatic ketone.

Names & identifiers

Preferred name: 2',4',6'-Trihydroxyacetophenone
IUPAC: 1-(2,4,6-trihydroxyphenyl)ethanone
English name: 2',4',6'-Trihydroxyacetophenone monohydrate
Molecular formula: C8H8O4
Molecular weight: 168.15

Names & synonyms

480-66-01-(2,4,6-Trihydroxyphenyl)ethanone2',4',6'-TrihydroxyacetophenonePHLOROACETOPHENONE2,4,6-TrihydroxyacetophenoneAcetophloroglucineAcetylphloroglucinol2-AcetylphloroglucinolEthanone, 1-(2,4,6-trihydroxyphenyl)-1-(2,4,6-Trihydroxyphenyl)ethan-1-one2,4,6-trihydroxy-acetophenone8L7XD8830T

Show more names

THAPPhloracetophenonePhloracetopheneMonoacetylphloroglucinol2-Acetylphloroglucinol hydrate2,4,6-trihydroxylacetophenone monohydrateNSC 54927

NSC-54927DTXSID5060061CHEBI:643441-(2,4,6-trihydroxyphenyl]ethanone2,4,6-THARefChem:861870DTXCID5040598207-556-5

Database identifiers

CAS: 480-66-0
PubChem CID: 68073
DTXSID: DTXSID5060061
ChEMBL: CHEMBL452477
ChEBI: CHEBI:64344
UNII: 8L7XD8830T
EC Number: 207-556-5
Nikkaji: J6.168I

Properties

Computed structural properties

XLogP: 1.1
Topological polar surface area: 77.8 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 4
Rotatable bonds: 1
Heavy atoms: 12
Formal charge: 0
Complexity: 168

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift

Endocrine DisruptorsPotential endocrine disrupting compound

Melting Point219 °C

Physical DescriptionSolid

Collision Cross Section · 2 items

129 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

126.29 Å² [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point: 219 · 219-221 °C(lit.)
Boiling point: 257.07 °C · 257.07°C (rough estimate)
Density: 1.3037 · 1.3037 (rough estimate)
refractive index: 1.509 · 1.5090 (estimate)
storage temp.: 30 °C · Store below +30°C.
solubility: DMSO (Sparingly), Ethanol (Slightly), Methanol (Slightly), Water (Very Slightly,
pka: 7.76 · 7.76±0.23(Predicted)
form: Powder
color: light yellow
Water Solubility: Soluble in water.
BRN: 1911197 · 1911197
Stability: Stable under recommended storage conditions., Stable Under Recommended Storage C
InChI: 1S/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3
InChIKey: XLEYFDVVXLMULC-UHFFFAOYSA-N
LogP: 1.472 · 1.472 (est)
CAS DataBase Reference: 480 · 480-66-0(CAS DataBase Reference)
FDA UNII: 8 L7XD8830T · 8L7XD8830T
NIST Chemistry Reference: 1 · Ethanone, 1-(2,4,6-trihydroxyphenyl)-(480-66-0)
EPA Substance Registry System: 1 · Ethanone, 1-(2,4,6-trihydroxyphenyl)- (480-66-0)
UNSPSC Code: 12352115 · 12352115
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 303 · H303-H315-H319-H335
Precautionary statements: 280 g-P261-P305+P351+P338 · P280g-P261-P305+P351+P338
target organs: Respiratory system
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36-24/25
WGK Germany: 3 · 3
RTECS: 528000 · AN0528000
TSCA: TSCA listed
HazardClass: IRRITANT
HS Code: 29145000 · 29145000
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk: 3
tsca: TSCA listed
rtecs: AN0528000
hs_code: 29145000
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36-24/25
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H303-H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P280g-P261-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

UsesSynthetic Polymer MALDI Matrix Compounds

General Manufacturing InformationEthanone, 1-(2,4,6-trihydroxyphenyl)-: ACTIVE

Applications · 2 items

UsesMonoacetylphloroglucinol (MAPG) is small molecular weight phenolic metabolite belonging to the phloroglucinol (1,3,5-trihydroxybenzene) family, produced by bacteria including Pseudomonas strains. MAPG exhibits a broad range of biological activity albeit with mostly low potency. In the search for novel actives, MAPG and related metabolites are important metabolites for dereplication to eliminate leads due to high amounts of weakly potent actives. Although weakly active, this family appears to be important in the biocontrol of plant diseases by some Pseudomonas strains.

UsesInduced choleresis in rats is mediated through multidrug resistance protein-2 (Mrp2). It enhances bile secretion.

Preparation methods · 1 item

PreparationPreparation by reaction of acetic anhydride on phloroglucinol,with concentrated sulfuric acid at 130° (70%)with boron trifluoride at 10° (62.5–68%) with zinc chloride at 145–150° (50%)with Amberlite IR-120 or Zeokarb 225 (cation exchange resins, sulfonic acid type) at 160° (39%).

Upstream & downstream products

Downstream products

3,4-Dimethoxyphenol 1-(3-ACETYL-2,4,6-TRIHYDROXYPHENYL)ETHAN-1-ONE Desmethylanhydroicaritin Licoflavone C 2-NITROPHLOROGLUCINOL 2',4',6'-TRIMETHOXYACETOPHENONE Isolicoflavonol Mulberrin 4-Ethylresorcinol 4H-1-Benzopyran-4-one, 5,8-dihydroxy-7-methoxy-2-(2-methoxyphenyl)-

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

南京兰亚化工贸易有限公司+86-25-8331-5620 · [email protected]

Additional notes · 1 item

DefinitionChEBI: A benzenetriol that is acetophenone in which the hydrogens at positions 2, 4, and 6 on the phenyl group are replaced by hydroxy groups. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of acid c glycans and glycopeptides.