Grundinformationen
- Standard-SMILES
O=C(O)c1ccc(O)c(O)c1- InChIKey
YQUVCSBJEUQKSH-UHFFFAOYSA-N- Summenformel
- C7H6O4
- Durchschnittliche Molmasse
- 154,12 g/mol
- Monoisotopische Masse
- 154,02660867
Überblick
3,4-dihydroxybenzoic acid is a dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. It has a role as an EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor, an antineoplastic agent, a plant metabolite, a human xenobiotic metabolite and an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor. It is a dihydroxybenzoic acid and a member of catechols. It is functionally related to a benzoic acid. It is a conjugate acid of a 3,4-dihydroxybenzoate.
Namen und Bezeichner
- Bevorzugter Name
- Protocatechuic Acid
- IUPAC
- 3,4-dihydroxybenzoic acid
- Lokaler Name
- 3,4-Dihydroxybenzoesure
- Englischer Name
- Protocatechuic acid
- Summenformel
- C7H6O4
- Molmasse
- 154.12
Namen und Synonyme
3,4-DIHYDROXYBENZOIC ACIDprotocatechuic acid99-50-34-Carboxy-1,2-dihydroxybenzeneProtocatehuic acid4,5-Dihydroxybenzoic acidDTXSID402121236R5QJ8L4BNSC-16631DTXCID601212FEMA NO. 4430CHEBI:36062
Weitere Namen anzeigen
Protocatechoic AcidHypogallic acid3,4-DihydroxybenzoicPROTOCATECHUIC ACID(P)Protocatechuic aci3,4-Dihydroxybenzoic acid,97%Pyrocatechol-p-carboxylic acid
RefChem:25857202-760-0protocatechuateBenzoic acid, 3,4-dihydroxy-3,4-DihydroxybenzoicacidMFCD000025093,4-Dihydroxy Benzoic Acidprotocatechuicacid
Datenbank-Bezeichner
- CAS
99-50-3- PubChem CID
- 72
- DTXSID
DTXSID4021212- ChEMBL
CHEMBL37537- ChEBI
CHEBI:36062- UNII
- 36R5QJ8L4B
- EC Number
- 202-760-0
- Nikkaji
- J11.618A
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,1
- Polarare Oberfläche (TPSA)
- 77,8 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 11
- Formalladung
- 0
- Komplexität
- 157
Experimentelle und physikochemische Eigenschaften
Chemical ClassesBiological Agents -> Plant Oils and Extracts
DrugsPharmaceuticals -> Listed in ZINC15
LogP0.86
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
18.2 mg/mL at 14 °C
Soluble
Soluble (in ethanol)
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point221 °C
Vapor Pressure0.0000021 [mmHg]
Physical Description
White to brownish solid; Discolored by air; [Merck Index]
Solid
Light brown solid
Dissociation Constants4.26 (at 25 °C)
Collision Cross Section
122.3 Ų [M+H-H2O]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
122.9 Ų [M-H]-
Physikochemische Eigenschaften
- Schmelzpunkt
- 197 · 197-200 °C (dec.) (lit.)
- Siedepunkt
- 237.46 °C · 237.46°C (rough estimate)
- Dichte
- 1.54 · 1.54
- Brechungsindex
- 1.64 · 1.6400 (estimate)
- FEMA
- 4430 · 4430 | 3,4-DIHYDROXYBENZOIC ACID
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 20 g/l · 20g/l
- pka
- 4.48 · 4.48(at 25℃)
- Aggregatzustand
- Fine Crystalline Powder
- Farbe
- Beige to brown
- PH
- 3.78 · 3.78(1 mM solution);3.25(10 mM solution);2.74(100 mM solution)
- Geruch (Odor)
- 100 % · at 100.00 %. mild phenolic balsamic
- Geruchsart
- phenolic
- Wasserlöslichkeit
- Soluble in hot alcohol and ether. Slightly soluble in water.
- Merck
- 14 · 14,7894
- JECFA Number
- 2278 · 2278
- BRN
- 1448841 · 1448841
- Stabilität
- Stable. Incompatible with strong oxidizing agents, strong bases.
- Kosmetik-Inhaltsstoffe Funktionen
- SKIN PROTECTING
- InChI
- 1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
- InChIKey
- YQUVCSBJEUQKSH-UHFFFAOYSA-N
- SMILES
- OC(=O)c1ccc(O)c(O)c1
- LogP
- 1.16 · 1.16
- CAS Datenbank
- 99 · 99-50-3(CAS DataBase Reference)
- EPA chemische Informationen
- Protocatechuic acid (99-50-3)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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 140 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Benzoic acid, 3,4-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses other liver changes and multiple enzyme effects in 28-day intermittent oral studies of rats; Intraperitoneal LD50 (mouse) > 800 mg/kg; [RTECS] A skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29182990
- RTECS-Nr.
- UL0560000
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
Metabolism/MetabolitesProtocatehuic acid is a known human metabolite of 3,4-dihydroxyphenylacetic acid.
MeSH Pharmacological ClassificationAgents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.
Tissue LocationsFibroblasts
Verwendung und Herstellung
Uses
Present in wheat grains and many other plants; [Merck Index]
Synthetic Polymer MALDI Matrix Compounds
Use Classification
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Anwendungen
Verwenden3,4-Dihydroxybenzoic Acid is a metabolite of polyphenols such as Phloretin (P339000) and Quercetin (Q509500).
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Ergänzende Hinweise
DefinitionChEBI: A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.
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