Curcumin

Curcumin

Enol form

Keto form

Title: Curcumin

CAS Registry Number: 458-37-7

CAS Name: (1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione

Additional Names: turmeric yellow; diferuloylmethane; C.I. 75300; C.I. Natural Yellow 3

Molecular Formula: C21H20O6

Molecular Weight: 368.38

Percent Composition: C 68.47%, H 5.47%, O 26.06%

Literature References: Natural dyestuff from root of Curcuma longa L., Zingiberaceae. Isoln: Vogel, Ann. 44, 297 (1842); Perkin, Phipps, J. Chem. Soc. (Trans.) 85, I, 64 (1904); Rao, Shintre, J. Soc. Chem. Ind. 47, 54T (1928). Synthesis: Lampe, Ber. 51,1347 (1918). Production: Stieglitz, Horn, DE 859145 (1952 to Hoechst). Biosynthesis studies: Roughley, Whiting, Tetrahedron Lett.1971, 3741. Chromatography: Srinivasan, J. Pharm. Pharmacol. 5, 448 (1953). See also: H. J. Conn's Biological Stains, R. D. Lillie, Ed. (Williams & Wilkins, Baltimore, 9th ed., 1977) pp 474-476. Pharmacology and anti-inflammatory activity: Srimal, Dhawan, ibid. 25, 447 (1973).

Properties: Orange-yellow, cryst powder, mp 183°. Insol in water, ether. Sol in alcohol, glacial acetic acid. Gives a brownish-red color with alkali; a light-yellow color with acids.

Melting point: mp 183°

Use: For preparing curcuma paper, pH range 8-9. In the detection of boron.

Curcumin

Curcumin

(458-37-7)

¹HNMR

H NMR spectrum of C21H20O6 in CDCL3 at 400 MHz.

Shifts

Index	Name	Shift (ppm)
11	HC6	7.392
24	HC7	6.767
13	HC1	7.583
15	HC	6.767
40	HC10	6.989
33	HC15	3.891
47	HC5	6.989
42	HC9	7.392
26	HC8	7.583
35	HC17	3.891
34	HC16	3.891
1	HC14	3.891
19	HC2	4.058
3	HC12	3.891
4	HC13	3.891
8	HC4	7.411
20	HC3	4.058
29	HC11	7.411

Figure 3. - Mass spectra of curcumin (A) and Cur-NPs (B). The mass spectra of curcumin and Cur-NPs were determined as described in Materials and methods.




Figure 4. - 1H-NMR spectra of curcumin (A) and Cur-NPs (B). The 1H-NMR spectra of curcumin and Cur-NPs were determined as described in Materials and methods.




Curcumin A structure was verified by nuclear magnetic resonance analysis (¹H-NMR) (CDCl₃, 400 MHz, ppm) δ 7.66 (d, J =15.6 Hz, 2H), 7.18 (dd, J =8.0, 1.6 Hz, 2H), 7.11 (d, J =2 Hz, 2H), 6.96 (d, J =1.6 Hz, 2H), 6.91 (d, J =9.6 Hz, 2H), 5.96 (s, 2H), 3.95 (s, 6H)

https://www.dovepress.com/inhibition-of-hiv-1-by-curcumin-a-a-novel-curcumin-analog-peer-reviewed-fulltext-article-DDDT

https://www.researchgate.net/publication/6490144_NMR_Study_of_the_Solution_Structure_of_Curcumin

NMR Study of the Solution Structure of Curcumin Article in Journal of Natural Products · March 2007 DOI: 10.1021/np060263s · Source: PubMed

http://iopscience.iop.org/article/10.1088/1757-899X/107/1/012063/pdf



SEE

Revisiting Curcumin Chemistry Part I: A New Strategy for the Synthesis ...

www.ncbi.nlm.nih.gov › NCBI › Literature › PubMed Central (PMC)

by EV Rao - ‎2011 - ‎Cited by 9 - ‎Related articles

A new strategy for the synthesis of curcuminoids is described involving the reaction of acetylacetone difluroboronite with an aromatic aldehyde in the presence of ...

[PDF]The Chemistry of Curcumin: From Extraction to Therapeutic Agent

www.mdpi.com/1420-3049/19/12/20091/pdf

by KI Priyadarsini - ‎2014 - ‎Cited by 42 - ‎Related articles

Dec 1, 2014 - analytical chemists. In organic chemistry the extraction and synthesis of curcumin and new synthetic derivatives was the main focus of research.

Isolation and synthesis of curcumin - ResearchGate

https://www.researchgate.net/file.PostFileLoader.html?id...assetKey...

May 31, 2012 - To obtain pure curcumin, column chromatography was needed ... steps fromcurcumin analogues, the synthesis was a faster way of obtaining ...

http://oasys2.confex.com/acs/236nm/techprogram/P1189704.HTM





http://www.mdpi.com/1420-3049/19/12/20091/htm








https://openi.nlm.nih.gov/detailedresult.php?img=PMC2674881_1471-2407-9-99-1&req=4

• Curcumin
• 
  
• 
  Synthesis of curcumin was first described by Lampe et al. In our laboratory curcumin has been synthesized by condensing vanillin (I) and acetyl acetone (II) in a medium of ethyl acetate using tributylborate as boron complex to avoid Knoevenagel condensation at C-3 of acetyl acetone. Curcumin is isolated from the reaction mixture by acidification and extraction with ethyl acetate. The organic layers are washed until neutral, dried and the solvent is removed. purified by chromatography over silica gel using ether/petroleum ether as the solvent.
• 
  Scrimal, R.C.; Curcumin. Drugs Fut 1987, 12, 4, 331
• Curcumin
• 
  
• 
  The protection of 4-bromo-2-methoxyphenol (I) with ethyl vinyl ether (II) and TsOH in dichloromethane gives the ethoxyethyl ether (III), which is treated with n-BuLi in THF to yield the phenyl lithium compound (IV). The reaction of (IV) with 2H-labeled DMF (V), followed by hydrolysis with HCl, affords the labeled 4-hydroxy-3-methoxybenzaldehyde (VI), which is finally condensed with pentane-2,4-dione (VII) by means of B2O3 and tetrahydroquinoline in DMF.
• 
  Threadgill, M.D.; Parveen, I.; Labelled compounds of interest as antitumour agents - VII. [H-2]- and [C-14]-curcumin. J Label Compd Radiopharm 2000, 43, 9, 883
• 
  Curcumin
• 
  
• 
  The protection of 4-bromo-2-methoxyphenol (I) with ethyl vinyl ether (II) and TsOH in dichloromethane gives the ethoxyethyl ether (III), which is treated with n-BuLi in THF to yield the phenyl lithium compound (IV). The reaction of (IV) with 14C-labeled DMF (V), followed by hydrolysis with HCl, affords the labeled 4-hydroxy-3-methoxybenzaldehyde (VI), which is finally condensed with pentane-2,4-dione (VII) by means of B2O3 and tetrahydroquinoline in DMF.
• 
  Threadgill, M.D.; Parveen, I.; Labelled compounds of interest as antitumour agents - VII. [H-2]- and [C-14]-curcumin. J Label Compd Radiopharm 2000, 43, 9, 883

https://www.researchgate.net/publication/224918513_Curcumin-From_Molecule_to_Biological_Function/figures?lo=1

Curcumin
	Scrimal, R.C.
	Drugs Fut 1987,12(4),331
Synthesis of curcumin was first described by Lampe et al. In our laboratory curcumin has been synthesized by condensing vanillin (I) and acetyl acetone (II) in a medium of ethyl acetate using tributylborate as boron complex to avoid Knoevenagel condensation at C-3 of acetyl acetone. Curcumin is isolated from the reaction mixture by acidification and extraction with ethyl acetate. The organic layers are washed until neutral, dried and the solvent is removed. purified by chromatography over silica gel using ether/petroleum ether as the solvent.

	Labelled compounds of interest as antitumour agents - VII. [H-2]- and [C-14]-curcumin
	Threadgill, M.D.; Parveen, I.
	J Label Compd Radiopharm 2000,43(9),883
The protection of 4-bromo-2-methoxyphenol (I) with ethyl vinyl ether (II) and TsOH in dichloromethane gives the ethoxyethyl ether (III), which is treated with n-BuLi in THF to yield the phenyl lithium compound (IV). The reaction of (IV) with 2H-labeled DMF (V), followed by hydrolysis with HCl, affords the labeled 4-hydroxy-3-methoxybenzaldehyde (VI), which is finally condensed with pentane-2,4-dione (VII) by means of B2O3 and tetrahydroquinoline in DMF.
The protection of 4-bromo-2-methoxyphenol (I) with ethyl vinyl ether (II) and TsOH in dichloromethane gives the ethoxyethyl ether (III), which is treated with n-BuLi in THF to yield the phenyl lithium compound (IV). The reaction of (IV) with 14C-labeled DMF (V), followed by hydrolysis with HCl, affords the labeled 4-hydroxy-3-methoxybenzaldehyde (VI), which is finally condensed with pentane-2,4-dione (VII) by means of B2O3 and tetrahydroquinoline in DMF.

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NMR from chemistrydept





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