Bisdemethoxycurcumin - Misplaced Pages

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Bisdemethoxycurcumin
Names

Preferred IUPAC name (1E,6E)-1,7-Bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
Other names Curcumin III, bis(4-hydroxycinnamoyl)methane, didemethoxycurcumin, bisdemethoxycurcumin, Bis(p-hydroxycinnamoyl)methane, NSC687839
Identifiers
CAS Number	24939-16-0
3D model (JSmol)	Interactive image
ChemSpider	4474770
PubChem CID	5315472
CompTox Dashboard (EPA)	DTXSID00872663
InChI InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+Key: PREBVFJICNPEKM-YDWXAUTNSA-N
SMILES C1=CC(=CC=C1C=CC(=O)CC(=O)C=CC2=CC=C(C=C2)O)O
Properties
Chemical formula	C₁₉H₁₆O₄
Molar mass	308.333 g·mol
Density	1.285 g/cm
Melting point	226 to 231 °C (439 to 448 °F; 499 to 504 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Bisdemethoxycurcumin is a curcuminoid found (along with the curcuminoids curcumin and demethoxycurcumin) in turmeric (Curcuma longa), but absent in Javanese turmeric (Curcuma xanthorrhiza). Bisdemethoxycurcumin is used as a pigment and nutraceutical with antimutagenic properties. All three of the curcuminoids found in Curcuma longa have been shown to have antioxidant properties, but bisdemethoxycurcumin is more resistant than the others to alkaline degradation. It was found to be effective in sensitizing PC cells resistance against gemcitabine.

References

T. K. Lim (11 February 2016). Edible Medicinal and Non-Medicinal Plants: Volume 12 Modified Stems, Roots, Bulbs. Springer. p. 374. ISBN 978-3-319-26065-5.
Hajime Ohigashi; Toshihiko Osawa; Junji Terao; Shaw Watanabe; Toshikazu Yoshikawa (27 November 2013). Food Factors for Cancer Prevention. Springer Science & Business Media. p. 251. ISBN 978-4-431-67017-9.
Jun-Ping Xu (25 November 2016). Cancer Inhibitors from Chinese Natural Medicines. CRC Press. p. 338. ISBN 978-1-4987-8766-6.
Francisco Delgado-Vargas; Octavio Paredes-Lopez (26 December 2002). Natural Colorants for Food and Nutraceutical Uses. CRC Press. p. 244. ISBN 978-1-4200-3171-3.
"Bisdemethoxycurcumin". ScienceDirect. ScienceDirect. Retrieved 5 October 2022.

External links

"TY000079". MassBank. MassBank Project. Archived from the original on 8 December 2015. Retrieved 3 May 2012.

v t e Curcuminoids
1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one Bisdemethoxycurcumin Curcumin Desmethoxycurcumin Dimethylcurcumin
Curcuminoid dyes	Rosocyanine Rubrocurcumin

v t e Antioxidants
Food antioxidants	6-Hydroxymelatonin Acetyl-L-carnitine (ALCAR) Alpha-lipoic acid (ALA) Ascorbic acid (vitamin C) Carotenoids (vitamin A) Curcumin Edaravone Polyphenols Glutathione Hydroxytyrosol L-carnitine Ladostigil Melatonin Mofegiline N-Acetylcysteine (NAC) N-Acetylserotonin (NAS) Oleocanthal Oleuropein Rasagiline Resveratrol Selegiline Selenium Tocopherols (vitamin E) Tocotrienols (vitamin E) Tyrosol Ubiquinone (coenzyme Q) Uric acid
Fuel antioxidants	Butylated hydroxyanisole Butylated hydroxytoluene 2,6-Di-tert-butylphenol 1,2-Diaminopropane 2,4-Dimethyl-6-tert-butylphenol Ethylenediamine
Measurements	Folin method ORAC TEAC FRAP

v t e Types of plant pigments
Betalains	Betacyanins Betaxanthins
Chlorophyll	Chlorophyll a Chlorophyll b Chlorophyll c Chlorophyll d Chlorophyll f Chlorin
Curcuminoids	1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one Bisdemethoxycurcumin Desmethoxycurcumin Curcumin
Flavonoids	Anthocyanins Anthocyanidins Anthoxanthins Flavans Condensed tannins
Carotenoids	Carotenes Retinoids Xanthophylls
Other	Allophycocyanin Phycocyanin Phycoerythrin Phycoerythrocyanin Quinones Xanthonoids

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