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  2. 99-50-3
Protocatechuic acid | 99-50-3

Product name:Protocatechuic acid

CAS No:99-50-3
MF:C7H6O4
MW:154.1201
MDL:MFCD00002509
CID:35022
PubChem ID:72
Introduction
      Protocatechuic acid, a water-soluble phenolic acid component, widely exists in common traditional Chinese medicines such as geranium, Salvia miltiorrhiza and classic compound preparations such as compound salvia miltiorrhiza injection and Guanxinning Injection. It not only significantly reduces myocardial oxygen consumption, improves myocardial oxygen tolerance and slows down heart rate, but also has definite antioxidant activity in vitro according to a large number of literatures
Names and Identifiers
  • 3,4-Dihydroxybenzoic acid
  • Protocatechuic acid
  • CATECHOL-4-CARBOXYLIC ACID
  • 3,4-DIHYDROXYBENZOIC ACID N-HYDRATE
  • 3,4-DIHYDROBENZOIC ACID
  • AKOS 220-70
  • RARECHEM AL BO 0347
  • PROTOCATECHUIC ACID N-HYDRATE
  • PROTOCATECHUIC ACID(P) PrintBack
  • PROTOCATECHUIC ACID(RG)
  • 2,4-Dihydroxybenzoic acid
  • 3,4-dihydroxybenzoate
  • 3,4-dihydroxy-benzoic acid
  • 4,5-Dihydroxybenzoic acid
  • 4-Carboxy-1,2-dihydroxybenzene
  • Benzoic acid,3,4-dihydroxy
  • protocatechuate
  • Protocatehuic acid
  • protochatechuic acid
  • Pyrocatechol-4-carboxylic Acid
  • 原儿茶酸
  • [ "" ]
  • Benzoic acid, 3,4-dihydroxy-
  • 3,4-Dihydroxybenzoicacid
  • 3, 4-Dihydroxybenzoic acid
  • MLS000737807
  • 36R5QJ8L4B
  • YQUVCSBJEUQKSH-UHFFFAOYSA-N
  • 1ykp
  • 3,4-dihydroxybenzoic acid (protocatechuic acid)
  • Protocatechuic acid polymer
  • 3,4-Dihydr
  • Catechol-4-carboxylic Acid
  • Protocatechuic Acid
  • SMR000528167
  • ConMedNP.2943
  • ConMedNP.2944
  • ConMedNP.2941
  • Dataset-S1.110
  • ConMedNP.2942
  • MLSMR
  • protocatechuic acid
  • MDL:MFCD00002509
  • InChIKey:YQUVCSBJEUQKSH-UHFFFAOYSA-N
  • Inchi:1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
  • SMILES:O([H])C1=C(C([H])=C([H])C(C(=O)O[H])=C1[H])O[H]
  • BRN:1448841
Chemical and Physical Properties

Computed Properties

  • Exact Mass: 154.12g/mol
  • Surface Charge: 0
  • XLogP3: 1.1
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Rotatable Bond Count: 1
  • Monoisotopic Mass: 154.026609g/mol
  • Monoisotopic Mass: 154.026609g/mol
  • Topological Polar Surface Area: 77.8Ų
  • Heavy Atom Count: 11
  • Complexity: 157
  • Isotope Atom Count: 0
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Covalently-Bonded Unit Count: 1
  • Topological Polar Surface Area: 77.8
  • Isotope Atom Count: 0
  • Tautomer Count: 12
  • XLogP4: 1.1
  • Surface Charge: 0

Experimental Properties

  • LogP: 0.79600
  • PSA: 77.76000
  • Merck: 7894
  • Refractive Index: 1.6400 (estimate)
  • Water Partition Coefficient: Soluble in hot alcohol and ether. Slightly soluble in water.
  • Boiling Point: 237.46°C (rough estimate)
  • Flash Point: 410.7 oC at 760 mmHg
  • FEMA: 4430 | 3,4-DIHYDROXYBENZOIC ACID
  • Color/Form: White to yellowish crystal powder
  • Stability/Shelf Life: Stable. Incompatible with strong oxidizing agents, strong bases.
  • Solubility: Soluble in hot water, ethanol and ether, slightly soluble in cold water, insoluble in benzene
  • Sensitiveness: Air Sensitive
  • pka: 4.48(at 25℃)
  • Density: 1.54
Security Information
  • Symbol: GHS07
  • RTECS:UL0560000
  • WGK Germany:3
  • Safety Instruction:S26-S36-S37/39
  • Risk Phrases:R36/37/38
  • खतरनाक माल साइन: Xi Xi
  • Hazardous Material transportation number:NONH for all modes of transport
  • Hazard Statement:H315,H319,H335
  • Warning Statement:P261,P305+P351+P338
  • Prompt:warning
  • Storage Condition:Powder -20°C 3 years   4°C 2 years In solvent -80°C 6 months   -20°C 1 month
  • Hazard Category Code:36/37/38
  • Signal Word:Warning
Customs Data
  • HS CODE:29182990
  • Customs Data:

    China Customs Code:

    2918290000

    Overview:

    2918290000 Other carboxylic acids and anhydrides containing phenolic groups but not other oxy groups\Acyl halide\Peroxides and peroxyacids and their derivatives.Regulatory conditions:AB(Customs clearance form for Inbound Goods,Customs clearance form for outbound goods).VAT:17.0%.Tax refund rate:9.0%.MFN tariff:6.5%.general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Regulatory conditions:

    A.Customs clearance form for Inbound Goods
    B.Customs clearance form for outbound goods

    Inspection and quarantine category:

    R.Sanitary supervision and inspection of imported food
    S.Sanitary supervision and inspection of exported food

    Summary:

    HS: 2918290000 other carboxylic acids with phenol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) VAT:17.0% MFN tariff:6.5% General tariff:30.0%

Synthetic Circuit

Synthetic Circuit 1

Reaction Conditions
1.1 Reagents: Potassium hydroxide ,  Potassium chloride ,  β-Cyclodextrin Solvents: Water
Reference
The influence of the host-guest interaction on the oxidation of natural flavonoid dyes
Ramesova, Sarka; et al, Collection of Czechoslovak Chemical Communications, 2011, 76(12), 1651-1667

Synthetic Circuit 2

Reaction Conditions
1.1 Reagents: Tetraethylammonium bromide ,  Potassium superoxide Solvents: Dimethylformamide ;  15 min, rt
1.2 18 h, rt
Reference
Reactivity pattern of in situ generated tetraethylammoniun superoxide with some flavonoids
Singh, Krishna Nand; et al, Indian Journal of Chemistry, 2007, (9), 1554-1557
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