flavan-4-ol

{{chembox

| Watchedfields = changed

| verifiedrevid = 445345071

| Name = Flavan-4-ol

| ImageFile = Flavan-4-ol.svg

| ImageName = Chemical structure of flavan-4-ol

| ImageFile2 = Flavan-4-ol 3D BS.png

| ImageName2 = Chemical structure of flavan-4-ol in ball-and-stick model

| IUPACName = Flavan-4-ol

| SystematicName = 2-Phenyl-3,4-dihydro-2H-1-benzopyran-4-ol

| OtherNames = 2-Phenylchroman-4-ol

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 487-25-2

| ChemSpiderID = 222586

| PubChem = 253959

| StdInChI=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

| StdInChIKey = YTMFRMLVZQOBDR-UHFFFAOYSA-N

| SMILES = C1C(C2=CC=CC=C2OC1C3=CC=CC=C3)O

}}

|Section2={{Chembox Properties

| C=15 | H=14 | O=2

| Density =

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| BoilingPt =

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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.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}} They can be found in the sorghum.{{cite journal|doi=10.1021/jf00006a035 | volume=39 | issue=6 | title=Flavan-4-ol concentration in leaf tissues of grain mold susceptible and resistant sorghum plants at different stages of leaf development | year=1991 | journal=Journal of Agricultural and Food Chemistry | pages=1163–1165 | last1 = Jambunathan | first1 = Ramamurthi | last2 = Kherdekar | first2 = Milind S.| url=http://oar.icrisat.org/2826/1/JA_1079.pdf }} 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.{{cite journal | doi = 10.1021/np050191p | volume=69 | issue=2 | title=Flavan-4-ol Glycosides from the Rhizomes of Abacopteris p enangiana | year=2006 | journal=Journal of Natural Products | pages=265–268 | last1 = Zhao | first1 = Zhongxiang| pmid=16499328 }}

Known flavan-4-ols

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.{{cite journal | doi = 10.1534/genetics.108.097170 | title = Progressive Loss of DNA Methylation Releases Epigenetic Gene Silencing from a Tandemly Repeated Maize Myb Gene | journal = Genetics | volume = 181 | pages = 81–91 | year = 2009 | last1 = Sekhon | first1 = Rajandeep S. | last2 = Chopra | first2 = Surinder | issue = 1 | pmid = 19001287 | pmc = 2621191 }}

References

{{reflist}}

{{Flavonoids}}

{{flavan-4ol}}