Bisdemethoxycurcumin

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−1
Density	1.285 g/cm3
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 [77 °F], 100 kPa). Infobox references

Bisdemethoxycurcumin is a curcuminoid found (along with the curcuminoids curcumin and demethoxycurcumin) in turmeric (Curcuma longa), but absent in Javanese turmeric (Curcuma xanthorrhiza).^[1] Bisdemethoxycurcumin is used as a pigment and nutraceutical with antimutagenic properties.^[2]^[3] 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.^[4] It was found to be effective in sensitizing PC cells resistance against gemcitabine.^[5]

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.

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

[Lim2016-1] 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.

[OhigashiOsawa2013-2] 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.

[Xu2016-3] Jun-Ping Xu (25 November 2016). Cancer Inhibitors from Chinese Natural Medicines. CRC Press. p. 338. ISBN 978-1-4987-8766-6.

[Delgado-VargasParedes-Lopez2002-4] 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.

[5] "Bisdemethoxycurcumin". ScienceDirect. ScienceDirect. Retrieved 5 October 2022.

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[5]

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

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⁻¹
Density	1.285 g/cm³
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 [77 °F], 100 kPa). Infobox references

Bisdemethoxycurcumin

See also

References

External links