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
Show more names
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
- Formal charge
- 0
- Complexity
- 124
Experimental & physicochemical properties
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.
- solubility
- 6.3 g/l · 6.3g/l
- form
- Crystalline Powder
- pka
- pK (25°) 7.55
- color
- slightly brown
- Odor
- 100 % · at 100.00 %. dry medicinal bitter almond
- Odor Type
- medicinal
- Water Solubility
- 50 g/L · 50 g/L (20 ºC)
- Sensitive
- Air Sensitive
- Merck
- 14 · 14,7893
- BRN
- 774381 · 774381
- Stability
- Stable. Incompatible with strong bases, strong oxidizing agents.
- Cosmetics Ingredients Functions
- BLEACHINGANTIOXIDANTSKIN CONDITIONING
- InChI
- 1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
- InChIKey
- IBGBGRVKPALMCQ-UHFFFAOYSA-N
- SMILES
- Oc1ccc(C=O)cc1O
- LogP
- 1.09 · 1.090
- CAS DataBase Reference
- 139 · 139-85-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4 PVP2HCH4T · 4PVP2HCH4T
- NIST Chemistry Reference
- 3 · 3,4-Dihydroxybenzaldehyde(139-85-5)
- EPA Substance Registry System
- 3 · Benzaldehyde, 3,4-dihydroxy- (139-85-5)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- 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 · 36/37/38-22
- Safety Statements
- 26 · 26-36-37/39
- WGK Germany
- 3 · 3
- RTECS
- 380000 · UL0380000
- F
- 9 · 9
- Hazard Note
- Irritant/Air Sensitive
- HS Code
- 29124900 · 29124900
- 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
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
Toxicology
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant/Air Sensitive
- 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
Pharmacology
Uses & manufacturing
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.
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: 3,4-dihydroxybenzaldehyde is a dihydroxybenzaldehyde.
Related reactions
Linked notes
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