5,5'-Dehydrodivanillate

CAS: 2134-90-9

Ref. 3D-FD71496

Product Information

• Name: 5,5'-Dehydrodivanillate
• Synonyms: 6,6'-Dihydroxy-5,5'-dimethoxybiphenyl-3,3'-dicarboxylic acid, 3,3′-Biphenyldicarboxylic acid, 6,6′-dihydroxy-5,5′-dimethoxy-, 6,6′-Dihydroxy-5,5′-dimethoxy[1,1′-biphenyl]-3,3′-dicarboxylic acid, 5,5′-Bivanillic acid, Dehydrodivanillic acid, [1,1′-Biphenyl]-3,3′-dicarboxylic acid, 6,6′-dihydroxy-5,5′-dimethoxy-

Description

5,5'-Dehydrodivanillate is an intermediate in the biosynthesis of vanillin from 5-carboxyvanillic acid. It is produced by the enzyme dehydrodivanillate synthase and converted to vanillin by the enzyme dehydrodivanillate reductase. The conversion of 5,5'-dehydrodivanillate to vanillin is an example of a radical coupling reaction. In plant cells, this intermediate is found in the cytoplasm and vacuoles. The uptake of 5,5'-dehydrodivanillate into plant cells has been shown to be facilitated by a transporter gene that is regulated by the presence of biphenyl or fatty acids. This function may be related to its role as an alternative substrate for olefin biosynthesis in plants. The dry weight of plant cells grown on 5,5'-dehydrodivanillate was shown to be greater than cells grown on other carbon sources

• Brand: Biosynth

Chemical properties

• Molecular weight: 334.28 g/mol
• Formula: C₁₆H₁₄O₈
• Purity: Min. 95%
• Color/Form: Powder
• InChI: InChI=1S/C16H14O8/c1-23-11-5-7(15(19)20)3-9(13(11)17)10-4-8(16(21)22)6-12(24-2)14(10)18/h3-6,17-18H,1-2H3,(H,19,20)(H,21,22)
• InChI key: InChIKey=QGCWGSXMGCSFDM-UHFFFAOYSA-N
• SMILES: COc1cc(C(=O)O)cc(-c2cc(C(=O)O)cc(OC)c2O)c1O