3,4-Dihydroxybenzaldehyde
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Basic information
- CAS
139-85-5- Standard SMILES
O=Cc1ccc(O)c(O)c1- InChIKey
IBGBGRVKPALMCQ-UHFFFAOYSA-N- Molecular formula
- C7H6O3
- Average molar mass
- 138.12 g/mol
- Monoisotopic mass
- 138.03169405
Overview
3,4-dihydroxybenzaldehyde is a dihydroxybenzaldehyde.
Names & identifiers
- Preferred name
- 3,4-Dihydroxybenzaldehyde
- IUPAC
- 3,4-dihydroxybenzaldehyde
- English name
- Protocatechualdehyde
- Molecular formula
- C7H6O3
- Molecular weight
- 138.12
Names & synonyms
3,4-DihydroxybenzaldehydeProtocatechualdehyde139-85-5PROTOCATECHUIC ALDEHYDERancinamycin IV4-Formyl-1,2-dihydroxybenzene3,4-Dihydroxybenzenecarbonal4PVP2HCH4TDTXSID4074512CHEBI:50205NSC-22961GM-W03
Show more names
3,4－Dihydroxybenzyl aldehydeNc 033NSC 22961AURORA 17180PROTOPINE(RG)rancinamyciniv
RefChem:45419DTXCID1034507O HUI WHITE EXTREME CELLIGHT205-377-7Benzaldehyde, 3,4-dihydroxy-catechaldehyde3,4-dihydroxy-benzaldehydeMFCD00003370
Database identifiers
- CAS
139-85-5- PubChem CID
- 8768
- DTXSID
DTXSID4074512- ChEMBL
CHEMBL222021- ChEBI
CHEBI:50205- UNII
- 4PVP2HCH4T
- EC Number
- 205-377-7
- Nikkaji
- J5.647B、J822.910D
Properties
Computed structural propertiesFilling in
- XLogP
- 1.3
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 124
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Benzaldehydes
DrugsPharmaceuticals -> Listed in ZINC15
LogP0.82
Flavoring AgentsEU Flavoring substances
Endocrine DisruptorsPotential endocrine disrupting compound
Vapor Pressure0.000116 [mmHg]
Physical DescriptionSolid; [Merck Index] Light brown powder; [Alfa Aesar MSDS]
Collision Cross Section126.83 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 150 · 150-157 °C(lit.)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 62.7% (89 of 142) of all reports.
Warning
H315 (34.5%): 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 142 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzaldehyde, 3,4-dihydroxy-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 13-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34350
3,4-Dihydroxybenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses convulsions and respiratory stimulation in intraperitoneal lethal-dose studies of mice (LD50 = 205 mg/kg); [RTECS] A skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (34.5%)
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Safety data
- F
- 9
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationAgents that prevent BLOOD CLOTTING.
Uses & manufacturing
UsesPresent in wheat grains and other plants; [ChemIDplus]
Applications
DescriptionProtocatechualdehyde is extracted from roots of the common traditional Chinese medicine Salvia miltiorrhiza Bge, which was harvested in autumn for better quality. Take root and remove stems, leaves and fibrous roots, then dry it. Most of them are wide, and they are mainly cultivated in recent years. South Salvia and Gansu Salvia are also widely used. Besides, there are a variety of sibling plant roots used as Salvia miltiorrhiza in Yunnan. Now, the existence of protocatechualdehyde has been found in variety of herbs, for example, in the leaf of Stenoloma Chusanum (L.) Ching and Ilex chinensis Sims.
HistoryIn the 1940s, the research was conducted overseas to obtain protocatechualdehyde form herbs. In 1972, the chemical group of Chinese herbal medicine in Nanjing College of Pharmacy systematically studied chemical composition in purple flower holly leaf and separated six monomers including protocatechualdehyde. Then they compared the effect of protocatechualdehyde, Salvia miltiorrhiza injection and hairy holly root injection, in which protocatechualdehyde is the most effective in increasing coronary sinus flow. Further experiments examined that protocatechualdehyde can increase coronary flow and improve coronary circulation, so it was called after perhexiline. Further clinical observation indicated that protocatechualdehyde has effect on coronary heart disease. The graduates of Nanjing College of Pharmacy in 1975 extracted, separated, isolated, and identified protocatechualdehyde in Salviamiltiorrhiza during the internship in Nanjing Municipal Hospital and studied its distribution, excretion, and toxicity in animals for clinical rational drug usage
Uses3,4-Dihydroxybenzaldehyde is used in as an apoptosis inducer of human leukemia cells.
Related reactions
207 records
Compound notes
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