Flavan-4-ol

Flavan-4-ol

Chemical structure of flavan-4-ol
Chemical structure of flavan-4-ol in ball-and-stick model
Names
IUPAC name Flavan-4-ol
Systematic IUPAC name 2-Phenyl-3,4-dihydro-2H-1-benzopyran-4-ol
Other names 2-Phenylchroman-4-ol
Identifiers
CAS Number	487-25-2^Y
3D model (JSmol)	Interactive image
ChemSpider	222586
PubChemCID	253959
InChI InChI=1S/C15H14O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-9,13,15-16H,10H2 Key: YTMFRMLVZQOBDR-UHFFFAOYSA-N
SMILES C1C(C2=CC=CC=C2OC1C3=CC=CC=C3)O
Properties
Chemical formula	C15H14O2
Molar mass	226.275 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

The flavan-4-ols (3-deoxyflavonoids) are flavone-derived alcohols and a family of flavonoids. Flavan-4-ols are colorless precursor compounds that polymerize to form red phlobaphene pigments.^[1] They can be found in the sorghum.^[2] Glycosides (abacopterins A, B, C and D together with triphyllin A and 6,8-dimethyl-7-hydroxy-4‘-methoxyanthocyanidin-5-O-β-d-glucopyranoside) can be isolated from a methanol extract of the rhizomes of Abacopteris penangiana.^[3]

Known flavan-4-ols

• Apiforol
• Luteoforol

Metabolism

Flavanone 4-reductase is an enzyme that uses (2S)-flavan-4-ol and NADP⁺ to produce (2S)-flavanone, NADPH, and H⁺.

Spectral data

These compounds have absorption maxima of 564 nm.^[4]

References

1. Styles, E. D., & Ceska, O. (1977). The genetic control of flavonoid synthesis in maize. Canadian Journal of Genetics and Cytology, 19(2), 289–302. doi:10.1139/g77-032
2. Jambunathan, Ramamurthi; Kherdekar, Milind S. (1991). "Flavan-4-ol concentration in leaf tissues of grain mold susceptible and resistant sorghum plants at different stages of leaf development"(PDF). Journal of Agricultural and Food Chemistry. 39 (6): 1163–1165. doi:10.1021/jf00006a035.
3. Zhao, Zhongxiang (2006). "Flavan-4-ol Glycosides from the Rhizomes of Abacopteris p enangiana". Journal of Natural Products. 69 (2): 265–268. doi:10.1021/np050191p. PMID 16499328.
4. Sekhon, Rajandeep S.; Chopra, Surinder (2009). "Progressive Loss of DNA Methylation Releases Epigenetic Gene Silencing from a Tandemly Repeated Maize Myb Gene". Genetics. 181 (1): 81–91. doi:10.1534/genetics.108.097170. PMC 2621191. PMID 19001287.