Protocatechualdehyde Basic information |
Product Name: | Protocatechualdehyde |
Synonyms: | AURORA 17180;AKOS BBS-00003254;3,4-DIHYDROXYBENZALDEHYDE;4-FORMYL-1,2-DIHYDROXYBENZENE;PROTOCATECHUALDEHYDE;PROTOCATECHUIC ALDEHYDE;1,2-Dihydroxy-4-formylbenzene;3,4-dihydroxy-benzaldehyd |
CAS: | 139-85-5 |
MF: | C7H6O3 |
MW: | 138.12 |
EINECS: | 205-377-7 |
Product Categories: | chemical reagent;pharmaceutical intermediate;Herb extract;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;FINE Chemical & INTERMEDIATES;Aromatic Aldehydes & Derivatives (substituted);BenzaldehydeDerivative;Benzaldehyde;aldehydes;Aromatics;Inhibitors |
Mol File: | 139-85-5.mol |
Protocatechualdehyde Chemical Properties |
Melting point | 150-157 °C(lit.) |
Boiling point | 213.5°C (rough estimate) |
density | 1.2667 (rough estimate) |
refractive index | 1.4600 (estimate) |
storage temp. | 2-8°C |
solubility | 6.3g/l |
pka | pK (25°) 7.55 |
form | Crystalline Powder |
color | slightly brown |
Water Solubility | 50 g/L (20 ºC) |
Sensitive | Air Sensitive |
Merck | 14,7893 |
BRN | 774381 |
Stability: | Stable. Incompatible with strong bases, strong oxidizing agents. |
CAS DataBase Reference | 139-85-5(CAS DataBase Reference) |
NIST Chemistry Reference | 3,4-Dihydroxybenzaldehyde(139-85-5) |
EPA Substance Registry System | Benzaldehyde, 3,4-dihydroxy- (139-85-5) |
Safety Information |
Hazard Codes | Xi |
Risk Statements | 36/37/38-22 |
Safety Statements | 26-36-37/39 |
WGK Germany | 3 |
RTECS | UL0380000 |
F | 9 |
Hazard Note | Irritant/Air Sensitive |
HS Code | 29124900 |
MSDS Information |
Provider | Language |
---|---|
Protocatechualdehyde | English |
SigmaAldrich | English |
ACROS | English |
ALFA | English |
Protocatechualdehyde Usage And Synthesis |
Description |
Is a phenolic aldehyde crystalline compound with the molecular formula C7H6O3. The compound is released from cork stoppers into wine. Also known as procatechuic aldehyde, protocatechualdehyde can be found in barley, grapevine, green Cavendish, and root of herb S. miltiorrhiza. The compound contains pro-apoptotic and antiproliferative properties against human breast cancer cells as well as colorectal cancer cells by reducing the expression of cyclin D1 and β-catenin. |
Chemical Properties | brown powder |
Synthesis Reference(s) | The Journal of Organic Chemistry, 27, p. 2037, 1962 DOI: 10.1021/jo01053a030 |
Enzyme inhibitor | This aldehyde (FW = 138.12 g/mol), also known as 3,4- dihydroxybenzaldehyde and 4-formylcatechol, is soluble in water (5 g/100 mL at 20°C) and has a pKa value of 7.55 at 25°C. Protocatechualdehyde induces apoptosis in cytotoxic T cells. Target(s): aldehyde oxidase; aldose reductase; b-carotene 15,15’-monooxygenase; mandelonitrile lyase; protocatechuate 3,4-dioxygenase; protocatechuate 4,5- dioxygenase; tyrosinase, weakly inhibited, IC50 = 620 μM; and xanthine oxidase. |
Purification Methods | Crystallise the aldehyde from water or toluene and dry it in a vacuum desiccator over KOH pellets or shredded wax respectively. [Beilstein 8 IV 1762.] |
Protocatechualdehyde Preparation Products And Raw materials |