Curcumin
Keto Form Enol Form
General
Systematic name	(1E,6E)-1,7-bis(4-hydroxy- 3-methoxyphenyl)-1,6- heptadiene-3,5-dione
Other names	curcumin diferuloylmethane C.I. 75300 Natural Yellow 3
Molecular formula	C21H20O6
SMILES	Oc1ccc(cc1OC)/C=C/C(=O)CC(=O)/C=C/c2ccc(O)c(OC)c2
Molar mass	368.38 g/mol
Appearance	?
CAS number	[458-37-7]
Properties
Density and phase	? g/cm³, ?
Solubility in water	? g/100 ml (? °C)
Melting point	? °C (? K)
Boiling point	? °C (? K)
Acidity (pKa)	?
Hazards
MSDS	External MSDS
Main hazards	?
NFPA 704
Flash point	? °C
R/S statement	R: ? S: ?
RTECS number	?
Related compounds
Related compounds	?
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Curcumin is the active ingredient of the Indian curry spice turmeric. It is a polyphenol with a molecular formula C₂₁H₂₀O₆. Curcumin can exist in at least two tautomeric forms, keto and enol. The keto form is preferred in solid phase and the enol form in solution. Curcumin structure. ... Enol form of curcumin. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... This article describes water from a scientific and technical perspective. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... In chemistry and biochemistry, the acid dissociation constant, the acidity constant, or the acid-ionization constant (Ka) is a specific type of equilibrium constant that indicates the extent of dissociation of hydrogen ions from an acid. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Binomial name Curcuma longa Linnaeus Turmeric (Curcuma longa, also known as tumeric) is a spice commonly used in curries and other South Asian cooking. ... Polyphenols are a group of plant chemical substances, characterized by the presence of more than one phenol group per molecule. ... Tautomers are organic compounds that are interconvertible by a chemical reaction called tautomerization. ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... Enol (or, more officially, but less commonly: alkenol) is an alkene with hydroxyl group on one of the carbon atoms of the double bond. ...

Curcumin can be used for boron quantification in the so-called curcumin method. It reacts with boric acid forming a red colored compound, known as rosocyanine. Boric acid, also called boracic acid or orthoboric acid, is a mild acid often used as an antiseptic, insecticide, flame retardant, in nuclear power plants to control the fission rate of uranium, and as a precursor of other chemical compounds. ... Rosocyanine and Rubrocurcumin are two red colored materials, which are formed by the reaction between curcumin and borates. ...

Curcumin is known for its antitumor, antioxidant, anti-amyloid and anti-inflammatory properties. Anti-inflammatory action may be due to leukotriene inhibition. To meet Wikipedias quality standards, this article or section can be improved by converting lengthy lists to text. ... Amyloid describes various types of protein aggregations that share specific traits when examined microscopically. ... Anti-inflammatory refers to the property of a substance or treatment that reduces inflammation. ...

Curcumin acts as a free radical scavenger and antioxidant, inhibiting lipid peroxidation and oxidative DNA damage. Curcuminoids induce glutathione S-transferase and are potent inhibitors of cytochrome P450. The Glutathione S-transferase (GST) family of enzymes comprises a long list of cytosolic, mitochondrial, and microsomal proteins which are capable of multiple reactions with a multitude of substrates, both endogenous and xenobiotic. ... Cytochrome P450 Oxidase (CYP2E1) Cytochrome P450 oxidase (commonly abbreviated CYP) is a generic term for a large number of related, but distinct, oxidative enzymes (EC 1. ...

For the last few decades, extensive work has been done to establish the biological activities and pharmacological actions of curcumin. Its anticancer effects stem from its ability to induce apoptosis in cancer cells without cytotoxic effects on healthy cells. Curcumin can interfere with the activity of the transcription factor NF-κB ( NF-kB ), which is often highly overexpressed in many cancer cells, according to a talk given by Dr. Dennis Liotta at Davidson College in January 2006. A cell undergoing apoptosis. ... NF-κB, or Nuclear Factor kappa B, is a nuclear transcription factor found in all cell types and is involved in cellular responses to stimuli such as stress, cytokines, free radicals, ultraviolet irradiation, and bacterial or viral antigens. ... Davidson College is a private liberal arts college for 1,700 students in Davidson, North Carolina. ...

A 2004 UCLA-Veterans Affairs study involving genetically altered mice suggests that curcumin might inhibit the accumulation of destructive beta-amyloid in the brains of Alzheimer's disease patients and also break up existing plaques associated with the disease. It was published that curcumin inhibits cyclooxygenase-2 (COX-2) as well as lipoxygenase (LOX), two enzymes involved in inflammation. Cyclooxygenase (COX) is an enzyme (EC 1. ... Lipoxygenases are a class of enzymes which add oxygen to lipids. ...

Curcumin, when eaten, is absorbed effectively as shown by the numerous studies and research on human and animal research. Since only one solitary study exists from 1998 on co-supplementation with piperine (extracted from black pepper), it does not appear to significantly increase the absorption of curcumin. It is not clear whether curcumin's beneficial effects require systemic absorption or not. Categories: Stub ...

It is used as a food coloring (it is what colors curry yellow). As a food additive, its E number is E100. Food coloring spreading on a soap bubble A food coloring is any substance that is added to food to change its color. ... Food additives are substances added to food to preserve flavour or improve its taste and appearance. ... For the mathematical constant see: E (mathematical constant). ... Binomial name Curcuma longa Linnaeus Turmeric (Curcuma longa, also known as tumeric or curcumin) is a spice commonly used in curries and other south Asian cooking. ...

However, as pointed out by Kawanishi et al. (2005) curcumin is a "double-edged sword" having both anti-cancer and carcinogenic effects. Carcinogenic effects are inferred from interference with the p53 tumor suppressor pathway, an important factor in human colon cancer. Carcinogenic and LD50 tests in mice and rats, however, have failed to establish a relationship between tumorogenesis and administration of curcumin in turmeric oleoresin at >98% concentrations.

Curcumin has devastating effects on healthy human cells. A study done by Kelly et al. (2001) in the journal of Mutation Research, proves that curcumin has prooxidant activity based on its effects on the DNA pattern achieved by alkaline gel electrophoresis. However, the undesired effects of curcumin can be suppressed by the lipophilic antioxidant α-tocopherol, a.k.a. vitamin E. The general structure of a section of DNA Deoxyribonucleic acid (DNA) is a nucleic acid that contains the genetic instructions for the biological development of a cellular form of life or a virus. ... Gel electrophoresis is a group of techniques used by scientists to separate molecules based on physical characteristics such as size, shape, or isoelectric point. ... A suppressor is a device attached to a gun to reduce the amount of noise generated by firing the weapon. ... This article or section does not cite its references or sources. ... α-Tocopherol (Vitamin E) Tocopherol, or vitamin E, is a fat-soluble vitamin in eight forms that is an important antioxidant. ...

There is also circumstantial evidence that curcumin improves mental functions; a survey of 1010 Asian people who ate yellow curry and were between the ages of 60 and 93 showed that those who ate the sauce "once every six months" or more had higher MMSE results than those who did not. From a scientific standpoint, though, this does not show whether the curry caused it, or people who had healthy habits also tended to eat the curry, or some completely different relationship.[1] Yellow curry is one of three major kinds of curry commonly used in Thailand, which are named for their color. ... MMSE can refer to: Mini mental state examination Minimum mean-square error estimation This is a disambiguation page — a navigational aid which lists other pages that might otherwise share the same title. ...

Asian curcumin may be toxic, not for the curcumin itself, but because of heavy metal, insecticide, herbicide and fungicide content. Those looking to curcumin for its admitted good effects may get unwelcome toxic companions from so-called "natural curcumin."

References

• Kelly, M.R., J. Xu, K.E. Alexander, and G. Loo. 2001. "Disparate effects of similar phenolic phytochemicals as inhibitors of oxidative damage to cellular DNA." Mutation Research. 485: 309-318. (PMID 11585363)

• Campbell, Frederick C.; Collett, Gavin P. 2005. "Chemopreventive properties of curcumin." Future Oncology, 1(3), 405-414. (PMID 16556014)

• Ringman, John M.; Frautschy, Sally A.; Cole, Gregory M.; Masterman, Donna L.; Cummings, Jeffrey L. "A potential role of the curry spice curcumin in Alzheimer's disease." Current Alzheimer Research, 2(2), 131-136. (PMID 15974909)

• Aggarwal, Bharat B.; Kumar, Anushree; Aggarwal, Manoj S.; Shishodia, Shishir. 2005. "Curcumin derived from turmeric (Curcuma longa): A spice for all seasons." Phytopharmaceuticals in Cancer Chemoprevention, 349-387.

• Chattopadhyay, Ishita; Biswas, Kaushik; Bandyopadhyay, Uday; Banerjee, Ranajit K. 2004. "Turmeric and curcumin: biological actions and medicinal applications." Current Science', 87(1), 44-53.

• Kawanishi, S. Oikawa, S. Murata, M. 2005. "Evaluation for safety of antioxidant chemopreventive agents." Antioxidants & Redox Signaling 7(11-12), 1728-1739. (PMID 16356133)

• Shoba G, Joy D, Joseph T, Majeed M, Rajendran R, Srinivas PS. 1998. "Influence Of Piperine On The Pharmacokinetics Of Curcumin In Animals And Human Volunteers". Planta medica, 64(4):353-6. (PMID 9619120)

• Moos PJ, Edes K, Mullally JE, Fitzpatrick FA. 2004 "Curcumin impairs tumor suppressor p53 function in colon cancer cells". Carcinogenesis, 25(9):1611-7. (PMID 15090465)

External links

• Journal of Biological Chemistry primary research article: Curcumin Inhibits Formation of Amyloid^β Oligomers and Fibrils, Binds Plaques, and Reduces Amyloid in Vivo
• Sloan-Kettering Herbal Guide
• Turmeric:Carcinogenic Potency Database