Curcumin

• CAS: 458-37-7
• Catalog Number: ACM458377
• Category: Inhibitors
• Molecular Weight: 368.38
• Molecular Formula: C21H20O6
• Description: Curcumin (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. As a food additive, its E number is E100.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. Although curcumin has been used historically in Ayurvedic medicine, there is no evidence from clinical research that it has medicinal properties.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.
• Synonyms: Diferulylmethane
• IUPAC Name: (1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)CC(=O)C=CC2=CC(=C(C=C2)O)OC)O
• InChI: InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+
• InChI Key: VFLDPWHFBUODDF-FCXRPNKRSA-N
• Boiling Point: 418.73 °C
• Melting Point: 183 °C
• Flash Point: 208.9±23.6 °C
• Density: 0.93 g/cm³
• Solubility: Insoluble in water
• Appearance: Solid
• Storage: 2-8 °C
• Active Content: 90%
• Complexity: 507
• EC Number: 203-984-1
• Exact Mass: 368.12598835
• Hazard Codes: Xi
• HS Code: 2932999099
• Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C(=O)CC(=O)/C=C/C2=CC(=C(C=C2)O)OC)O
• LogP: 3.85260
• MDL Number: MFCD00004885
• Monoisotopic Mass: 368.12598835
• Physical State: Solid
• pKa: 8.09(at 25 °C)
• PSA: 96.22
• Refractive Index: 1.4155-1.4175
• Solubility In Water: Slightly
• Stability: Stable, but may be light sensitive. Incompatible with strong oxidizing agents.
• Storage Conditions: -20ºC
• Topological Polar Surface Area: 93.1 Ų
• Vapor Density: 13
• Vapor Pressure: 6.43E-15mmHg at 25°C
• WGK Germany: 2

Synthetic Use

Upstream Synthesis Route 1

• 30802-02-9
• 524-14-1

• 1080-12-2
• 458-37-7

Reference: [1] RSC Advances, 2016, vol. 6, # 15, p. 12519 - 12524

Upstream Synthesis Route 2

• 121-33-5
• 123-54-6

• 458-37-7

Reference: [1] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 22, p. 11041 - 11046

Upstream Synthesis Route 3

• 121-33-5

• 458-37-7

Reference: [1] Patent: US2006/160812, 2006, A1, . Location in patent: Page/Page column 2

Downstream Synthesis Route 1

• 458-37-7

• 36062-04-1

Reference: [1]Patent: CN104496779,2017,B .Location in patent: Paragraph 0014; 0015; 0016; 0017; 0018-0023

Downstream Synthesis Route 2

• 108-55-4
• 458-37-7

• 1000878-09-0

Reference: [1]Liu, Bingmi; Xia, Mingyu; Ji, Xiaoling; Xu, Liying; Dong, Jinhua
[Chemical and Pharmaceutical Bulletin, 2013, vol. 61, # 7, p. 757 - 763]

* For details of the synthesis route, please refer to the original source to ensure accuracy.