3,4-Dihydroxybenzaldehyde

Base Information

• Chemical Name: 3,4-Dihydroxybenzaldehyde
• CAS No.: 139-85-5
• Molecular Formula: C7H6O3
• Molecular Weight: 138.123
• Hs Code.: 29124900
• European Community (EC) Number: 205-377-7
• NSC Number: 22961
• UNII: 4PVP2HCH4T
• DSSTox Substance ID: DTXSID4074512
• Nikkaji Number: J5.647B,J822.910D
• Wikipedia: Protocatechuic_aldehyde
• Wikidata: Q411602
• Metabolomics Workbench ID: 57367
• ChEMBL ID: CHEMBL222021
• Mol file: 139-85-5.mol

Synonyms:3,4-dihydroxybenzaldehyde;protocatechualdehyde;protocatechualdehyde, 3H-labeled;protocatechualdehyde, formyl-14C-labeled;protocatechuic aldehyde;rancinamycin IV

Chemical Property of 3,4-Dihydroxybenzaldehyde

Chemical Property:

• Appearance/Colour: brown powder
• Vapor Pressure: 0.000867mmHg at 25°C
• Melting Point: 150-157 °C(lit.)
• Refractive Index: 1.674
• Boiling Point: 295.4 °C at 760 mmHg
• PKA: pK (25°) 7.55
• Flash Point: 146.7 °C
• PSA: 57.53000
• Density: 1.409 g/cm³
• LogP: 0.91030
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: 6.3g/l
• Water Solubility.: 50 g/L (20 ºC)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 138.031694049
• Heavy Atom Count: 10
• Complexity: 124

Purity/Quality:

≥99% ^*data from raw suppliers

Protocatechualdehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Benzaldehydes
• Canonical SMILES: C1=CC(=C(C=C1C=O)O)O
• Description: Protocatechualdehyde 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.
• Physical properties: Appearance: pale beige acicular crystal (in water or methylbenzene) or off-white powder, crystal twin shape. Solubility: easily soluble in ethanol, acetone, ethyl acetate, ethyl ether, and hot water; soluble in cold water; insoluble in benzene and chloroform. Melting point: 150–153?°C. Specific optical rotation: easily oxidized to benzoquinone and changes color, and it is instable in water.
• Uses: 3,4-Dihydroxybenzaldehyde is used in as an apoptosis inducer of human leukemia cells. 3,4-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.
• Clinical Use: Perhexiline injection containing protocatechualdehyde 100? mg/2? mL by intravenous infusion or intramuscular injection was used to treat coronary heart disease, chest tightness, angina, and myocardial infarction. Injection treats ischemic stroke and improves both symptoms and signs of patients. Treating chronic hepatitis and early cirrhosis: relieving the symptoms, promoting the recovery of liver function, and hepatosplenomegaly. It can significantly improve the blood rheology index for patients with acute exacerbation of chronic pulmonary heart disease. Treatment of peptic ulcer: a certain effect. Others: it has effect on many diseases like viral myocarditis, embolism of central retinal artery, thromboangiitis obliterans, scleredema neonatorum, scleroderma, psoriasis, nerve deafness, and toxemia of pregnancy.

Technology Process of 3,4-Dihydroxybenzaldehyde

There total 113 articles about 3,4-Dihydroxybenzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

3,4-dimethoxy-benzaldehyde (120-14-9) → isovanillin (621-59-0) + vanillin (121-33-5,8014-42-4) + 3,4-dihydroxybenzaldehyde (139-85-5)

Guidance literature:

With orcinol; Acetobacterium dehalogenans veratrol-O-demethylase; Desulfitobacterium hafniense methyltransferase dhaf4611; In aq. buffer; at 35 ℃; for 24h; pH=6.5; regioselective reaction; Inert atmosphere; Enzymatic reaction;

DOI:10.1021/acscatal.0c02790

Reference yield: 58.0%

3,4-dimethoxy-benzaldehyde (120-14-9) → vanillin (121-33-5,8014-42-4) + 3,4-dihydroxybenzaldehyde (139-85-5)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol; for 0.25h; Heating;

DOI:10.1021/jo0256540

Reference yield: 0.04%

D-erythrose (583-50-6) → 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + 3,4-Dihydroxybenzoic acid (99-50-3) + 1-(3,4-dihydroxyphenyl)ethan-1-one (1197-09-7) + 1-[5-(hydroxymethyl)furan-2-yl]ethan-1-one (55087-82-6) + 3,4-dihydroxybenzaldehyde (139-85-5) + 3-methylbenzene-1,2-diol (488-17-5)

Guidance literature:

With acetate buffer; for 45h; Product distribution; Heating;

upstream raw materials:

isovanillin

methanol

sodium methylate

N-Bromosuccinimide

Downstream raw materials:

(Z)-2-(3,4-dihydroxybenzylidene)-6-methoxybenzofuran-3(2H)-one

3,4-bis(ethoxycarboxy)-benzaldehyde

3,4-dibenzoyloxybenzaldehyde

3-hydroxy-4-n-propoxy-benzaldehyde

Refernces

• 1、 Jovanovic, Slobodan V.,Steenken, Steen,Tosic, Mihajlo,Marjanovic, Budimir,Simic, Michael G.. "Flavonoids as antioxidants". . p. 4846 - 4851. Retrieved 1994.
• 2、 Hossain, Md. Mokarrom,Aldous, Leigh. "Polyoxometalates as solution-phase electrocatalytic mediators for reduced electrode fouling and the improved oxidative response of phenols". . p. 32 - 35. Retrieved 2016.
• 3、 Zaghouani, Mehdi,B?geholz, Lena A.K.,Mercier, Evan,Wintermeyer, Wolfgang,Roche, Stéphane P.. "Total synthesis of (±)-fumimycin and analogues for biological evaluation as peptide deformylase inhibitors". . p. 3216 - 3230. Retrieved 2019.
• 4、 Grimm, Christopher,Kroutil, Wolfgang,Pompei, Simona,Schiller, Christine,Schober, Lukas. "Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives". supporting information. p. 16906 - 16910. Retrieved 2021/07/02.
• 5、 -. "A method of synthesis of piperonolamine". Paragraph 0112; 0116-0118; 0128; 0132-0134. . Retrieved 2022/01/07.