Curcumin (/krkjumn/, diferuloylmethane) is a bright yellow chemical produced by some plants.

It
is the principal curcuminoid of turmeric (Curcuma longa), a member of the ginger family
(Zingiberaceae). It is sold as an herbal supplement, cosmetics ingredient, food flavoring, and food
coloring.[1] As a food additive, its E number is E100.[2]

It was isolated in 1815 when Vogel and Pelletier reported the isolation of a "yellow coloring-matter"
from the rhizomes of turmeric and named it curcumin.[3] Although curcumin has been used historically
in Ayurvedic medicine,[4] its potential for medicinal properties remains unproven and is questionable
as a therapy when used orally.[5][6][7]

Chemically, curcumin is a diarylheptanoid, belonging to the group of curcuminoids, which are natural
phenols responsible for turmeric's yellow color. It is a tautomeric compound existing in enolic form in
organic solvents and as a keto form in water.[8]

The most common applications are as a dietary supplement, in cosmetics, as a food coloring, and as
flavoring for foods such as turmeric-flavored beverages (Japan). [1]

Curcumin

Annual sales of curcumin have increased since 2012, largely due to an increase in its popularity as a
dietary supplement.[1] It is increasingly popular in skin care products that are marketed as containing
natural ingredients or dyes, especially in Asia.[1] The largest market is in North America, where sales
exceeded US$20 million in 2014.[1]

Chemistry[edit]

Curcumin incorporates several functional groups whose structure was first identified in 1910. [9] The
aromatic ring systems, which are phenols, are connected by two ,-unsaturated carbonyl groups.
The diketones form stable enols and are readily deprotonated to form enolates; the ,-unsaturated
carbonyl group is a good Michael acceptor and undergoes nucleophilic addition.

Curcumin is used as an indicator for boron.[10] It reacts with boric acid to form a red-color
compound, rosocyanine.
Biosynthesis[edit]

The biosynthetic route of curcumin is uncertain. In 1973, Roughly and Whiting proposed two
mechanisms for curcumin biosynthesis. The first mechanism involves a chain extension reaction
by cinnamic acid and 5 malonyl-CoA molecules that eventually arylized into a curcuminoid. The
second mechanism involves two cinnamate units coupled together by malonyl-CoA. Both use
cinnamic acid as their starting point, which is derived from the amino acid phenylalanine.[11]

Plant biosyntheses starting with cinnamic acid is rare compared to the more common p-coumaric
acid.[11] Only a few identified compounds, such as anigorufone and pinosylvin, build from cinnamic
acid.[12][13]