Basic information
- CAS
3943-89-3- Standard SMILES
CCOC(=O)c1ccc(O)c(O)c1- InChIKey
KBPUBCVJHFXPOC-UHFFFAOYSA-N- Molecular formula
- C9H10O4
- Average molar mass
- 182.17 g/mol
- Monoisotopic mass
- 182.0579088
Overview
Ethyl 3,4-dihydroxybenzoate is an ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol. It is the anti-oxidative component of peanut seed testa. It has a role as an EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor, an antioxidant, an antibacterial agent, an apoptosis inducer and a plant metabolite. It is an ethyl ester and a member of catechols. It is functionally related to a 3,4-dihydroxybenzoic acid.
Names & identifiers
- Preferred name
- Ethyl 3,4-Dihydroxybenzoate
- IUPAC
- ethyl 3,4-dihydroxybenzoate
- English name
- Ethyl 3,4-dihydroxybenzoate
- Molecular formula
- C9H10O4
- Molecular weight
- 182.17
Names & synonyms
Ethyl 3,4-dihydroxybenzoate3943-89-3Ethyl protocatechuateProtocatechuic acid ethyl ester3,4-Dihydroxybenzoic Acid Ethyl EsterEthyl-3,4-dihydroxybenzoateDTXSID20577324YGJ96WTBGNSC-86130DTXCID3031521CHEBI:132364RefChem:138647
Show more names
NSC 86130NSC 6196813,4-2-ethylERLOTINIBINT-ARARECHEM AL BI 0069Ethyl 3,4-dihydroxyb
223-529-0Benzoic acid, 3,4-dihydroxy-, ethyl esterMFCD00002199Erlotinib Impurity 55CHEMBL4862163,4-Dihydroxy-benzoic acid ethyl esterEDHBUNII-4YGJ96WTBG
Database identifiers
- CAS
3943-89-3- PubChem CID
- 77547
- DTXSID
DTXSID2057732- ChEMBL
CHEMBL486216- ChEBI
CHEBI:132364- UNII
- 4YGJ96WTBG
- EC Number
- 223-529-0
- Nikkaji
- J208.318C
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 180
Physicochemical properties
- Melting point
- 132 · 132-134 °C(lit.)
- Boiling point
- 275.56 °C · 275.56°C (rough estimate)
- Density
- 1.2481 · 1.2481 (rough estimate)
- vapor pressure
- 0 · 0-9.4Pa at 20-120℃
- refractive index
- 1.45 · 1.4500 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Crystalline Powder
- pka
- 8.19 · 8.19±0.18(Predicted)
- color
- Pale yellow to beige
- Odor
- 100 % · at 100.00%. phenolic
- Water Solubility
- Insoluble in water. Soluble in ethanol.
- BRN
- 2097435 · 2097435
- Cosmetics Ingredients Functions
- ANTIOXIDANTSKIN CONDITIONING - MISCELLANEOUSANTIMICROBIAL
- InChI
- 1S/C9H10O4/c1-2-13-9(12)6-3-4-7(10)8(11)5-6/h3-5,10-11H,2H2,1H3
- InChIKey
- KBPUBCVJHFXPOC-UHFFFAOYSA-N
- SMILES
- CCOC(=O)c1ccc(O)c(O)c1
- LogP
- 1.4 at · 1.4 at 35℃ and pH6.6
- Surface tension
- 74.7 mN/m · 74.7mN/m at 1g/L and 20℃
- CAS DataBase Reference
- 3943 · 3943-89-3(CAS DataBase Reference)
- FDA UNII
- 4 YGJ96WTBG · 4YGJ96WTBG
- NIST Chemistry Reference
- 3 · Benzoic acid, 3,4-dihydroxy-, ethyl ester(3943-89-3)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-37/39
- WGK Germany
- 3 · 3
- Hazard Note
- Irritant
- HS Code
- 29053990 · 29053990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (95.4%): 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 87 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 04-10-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/18793
Hazard Classes and CategoriesSkin Irrit. 2 (95.4%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29053990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36-37/39
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Use ClassificationFood Additives -> ANTIOXIDANT -> JECFA Functional Classes
Applications
DescriptionEthyl 3,4-dihydroxybenzoate (EDHB) is an analogue of 2-oxoglutarate and thus a competitive inhibitor of prolyl hydroxylase domain enzymes (PHDs). It is known as protocatechuic acid and is present in plant foods such as olives, roselle, du-zhong, and white grape wine.This compound have antioxidant, cardioprotective, neuroprotective, antimicrobial, anti-inflammatory and myoprotective activity, as well as anti-ulcer activity[1].
UsesAn antioxidant compound found in Sicilian virgin olive oils and red wines.
UsesThe compound is a prolyl 4-hydroxylase inhibitor and can be used to protect the myocardium.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
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Additional notes
DefinitionChEBI: An ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol. It is the anti-oxidative component of peanut seed testa.
Related reactions
91 records
Compound notes
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