3,4-Dihydroxybenzaldehyde

HCID 8768CAS 139-85-5

Basic information

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 properties

XLogP
1.3
Topological polar surface area
57.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
10

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]

Physicochemical properties

Melting point
150 · 150-157 °C(lit.)
Boiling point
213.5 °C · 213.5°C (rough estimate)
Density
1.2667 · 1.2667 (rough estimate)
refractive index
1.46 · 1.4600 (estimate)
FLAVIS Number
5.142 · 05.142 | 3,4-Dihydroxybenzaldehyde
storage temp.
30 °C · Store below +30°C.

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 4 items

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
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
UL0380000
hs_code
29124900
risk_code
36/37/38-22

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationAgents that prevent BLOOD CLOTTING.

Uses & manufacturing

UsesPresent in wheat grains and other plants; [ChemIDplus]
Applications · 5 items

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.

Uses3,4-Dihydroxybenzaldehyde may be used for the surface modification of nanocrystalline TiO2 particles. Electrodeposited layer of 3,4-dihydroxybenzaldehyde may be used as effective redox mediator during oxidation of NADH at graphene. It may be used in the preparation of new diSchiff base ligands, which forms di-, tri- and tetranuclear Co(II) and Cu(II) complexes.

General Description3,4-Dihydroxybenzaldehyde has been recognized as one of the antifungal compound extracted from the outer skin of green Cavendish bananas. It can be synthesized from catechol via Fries rearrangement.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京一化生物科技有限公司13429882898; 13429882898

Additional notes

DefinitionChEBI: 3,4-dihydroxybenzaldehyde is a dihydroxybenzaldehyde.

Related reactions

207 records

Linked notes

Loading…