3,4-Dihydroxybenzaldehyde

Names

[ CAS No. ]:
139-85-5

[ Name ]:
3,4-Dihydroxybenzaldehyde

[Synonym ]:
Benzaldehyde, 3,4-dihydroxy-
1,2-dihydroxy-4-formylbenzene
3,4-Dihydroxy benzaldehyde
4-formyl-1,2-benzenediol
3,4-Dihydroxybenzyl aldehyde
RANCINAMYCIN IV
MFCD00003370
UNII-4PVP2HCH4T
4-formyl-1,2-dihydroxybenzene
EINECS 205-377-7
3,4-Dihydroxybenzaldehyde
Protocatechuic aldehyde
Protocatechualdehyde

Biological Activity

[Description]:

Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Others >> Others

[In Vitro]

Protocatechualdehyde (PCA) (50, 100 μM, 24/48 hours ) treated MCF-7 cells significantly decrease cell growth by 11% and 20% in 24 hours and by 22% and 27% in 48 hours, respectively[2]. Protocatechualdehyde (50, 100 μM, 24 hours) treated MCF-7 cells are increased by 1.9-fold and 2.6-fold in the concentrations of 50 μM and 100 μM, respectively. PCA suppresses proliferation of estrogen receptor (ER)-positive (MCF-7) breast cancer cells, but not ER-negative (MDA-MB-231) breast cancer cells[2]. Protocatechualdehyde (0, 100, 200 μM, 48 hours in HCT116 and SW480 cells) affects the enzyme activity of HDAC and observed that PCA treatment resulted in inhibition of HDAC activity in dose-dependent manner[3]. Cell Proliferation Assay[2] Cell Line: Human breast cancer cell (MCF-7 and MDA-MB-231) Concentration: 0, 5, 10, 25, 50, and 100 μM Incubation Time: 24, 48 hours Result: inhibited MCF-7 cells cell growth. Apoptosis Analysis[2] Cell Line: Human breast cancer cell (MCF-7 and MDA-MB-231) Concentration: 0, 5, 10, 25, 50, and 100 μM Incubation Time: 24, 48 hours Result: increased apoptosis in MCF-7 cells.

[References]

[1]. Li S, et al. Evaluation of the Antibacterial Effects and Mechanism of Action of Protocatechualdehyde against Ralstonia solanacearum. Molecules. 2016 Jun 9;21(6).

[2]. Choi J, et al. Anticancer activity of protocatechualdehyde in human breast cancer cells. J Med Food. 2014 Aug;17(8):842-8.

[3]. Jeong JB, et al. Protocatechualdehyde possesses anti-cancer activity through downregulating cyclin D1 and HDAC2 in human colorectal cancer cells. Biochem Biophys Res Commun. 2013 Jan 4;430(1):381-6.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
295.4±20.0 °C at 760 mmHg

[ Melting Point ]:
150-157 °C(lit.)

[ Molecular Formula ]:
C₇H₆O₃

[ Molecular Weight ]:
138.12

[ Flash Point ]:
146.7±18.3 °C

[ Exact Mass ]:
138.031693

[ PSA ]:
57.53000

[ LogP ]:
1.14

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.674

[ Storage condition ]:
2-8°C

[ Stability ]:
Stable. Incompatible with strong bases, strong oxidizing agents.

[ Water Solubility ]:
50 g/L (20 ºC)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UL0380000

CHEMICAL NAME :: Protocatechualdehyde

CAS REGISTRY NUMBER :: 139-85-5

LAST UPDATED :: 198311

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C7-H6-O3

MOLECULAR WEIGHT :: 138.13

WISWESSER LINE NOTATION :: VHR CQ DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 205 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: APFRAD Annales Pharmaceutiques Francaises. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1943- Volume(issue)/page/year: 15,461,1957

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 56 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#07875

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UL0380000

[ HS Code ]:
29124900

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2912499000

[ Summary ]:
2912499000. other aldehyde-ethers, aldehyde-phenols and aldehydes with other oxygen function. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:5.5%. General tariff:30.0%

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Bioorg. Med. Chem. 15 , 2006-15, (2007)

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Chromatographic evaluation and QSAR optimization for benzoic acid analogues against carbonic anhydrase III.

J. Enzyme Inhib. Med. Chem. 30 , 420-9, (2015)

An HPLC-size exclusion method was developed as an assay method to evaluate the binding of tested compounds with carbonic anhydrase III (CAIII) enzyme. Inhibition of CAIII by a group of benzoic acid an...

Related Compounds

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