Protocatechuic acid

Protocatechuic acid
Names
Preferred IUPAC name
3,4-Dihydroxybenzoic acid
Other names
3,4-Dihydroxybenzoic acid
PCA
Protocatechuate
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.509 Edit this at Wikidata
EC Number
  • 202-760-0
KEGG
RTECS number
  • UL0560000
UNII
  • InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11) checkY
    Key: YQUVCSBJEUQKSH-UHFFFAOYSA-N checkY
  • C1=CC(=C(C=C1C(=O)O)O)O
Properties
C7H6O4
Molar mass 154.12 g/mol
Appearance light brown solid
Density 1.524 g/cm3 (4 °C)[1]
Melting point 202 °C (396 °F; 475 K)[1]
18 g/L (14 °C)
271 g/L (80 °C)[2]
Solubility soluble in ethanol, ether
insoluble in benzene
Acidity (pKa) 4.48, 8.83, 12.6[3]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
UV visible spectrum of protocatechuic acid

Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies.[4] It is produced commercially from vanillin.[5]

  1. ^ a b Haynes, p. 3.190
  2. ^ Haynes, p. 5.148
  3. ^ Haynes, p. 5.91
  4. ^ Lin, H.-H.; Chen, J.-H.; Huang, C.-C.; Wang, C.-J. (June 2007). "Apoptotic effect of 3,4-dihydroxybenzoic acid on human gastric carcinoma cells involving JNK/p38 MAPK signaling activation". International Journal of Cancer. 120 (11): 2306–2316. doi:10.1002/ijc.22571. PMID 17304508.
  5. ^ Ritzer, Edwin; Sundermann, Rudolf (2000). "Hydroxycarboxylic Acids, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_519. ISBN 3527306730.