Curcumin

Base Information

• Chemical Name: Curcumin
• CAS No.: 458-37-7
• Deprecated CAS: 15845-47-3,33171-04-9,73729-23-4,79257-48-0,91884-86-5,2103286-06-0,33171-04-9,73729-23-4,79257-48-0,91884-86-5
• Molecular Formula: C21H20O6
• Molecular Weight: 368.386
• Hs Code.: 29145000
• European Community (EC) Number: 207-280-5
• NSC Number: 687842,32982
• UNII: IT942ZTH98
• DSSTox Substance ID: DTXSID8031077
• Nikkaji Number: J1.391.353F,J5.762B
• Wikipedia: Curcumin
• Wikidata: Q312266
• NCI Thesaurus Code: C401
• RXCUI: 2955
• Pharos Ligand ID: PU7DU4ZZ438B
• Metabolomics Workbench ID: 38100
• ChEMBL ID: CHEMBL140
• Mol file: 458-37-7.mol

Synonyms:1,6-Heptadiene-3,5-dione,1,7-bis(4-hydroxy-3-methoxyphenyl)-, (E,E)- (8CI);Curcumin (6CI);(1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione;(E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione;(E,E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione;C Yellow 15;C.I. 75300;C.I. Natural Yellow 3;Curcuma;Curcumin I;Diferuloylmethane;E 100;E 100 (dye);Halud;IndianSaffron;Kacha Haldi;Merita Earth;NSC 32982;San-Ei Curcumine AL;San-Ei Gen Curcumine AL;Terra Merita;Turmeric;Turmeric yellow;Ukon (dye);Yellow Ginger;trans,trans-Curcumin;Curcumin;

Chemical Property of Curcumin

Chemical Property:

• Appearance/Colour: orange crystalline powder
• Vapor Pressure: 6.43E-15mmHg at 25°C
• Melting Point: 183 °C
• Refractive Index: 1.4155-1.4175
• Boiling Point: 591.4 °C at 760 mmHg
• PKA: 8.09(at 25℃)
• Flash Point: 208.9 °C
• PSA: 96.22000
• Density: 1.279 g/cm³
• LogP: 3.85260
• Storage Temp.: −20°C
• Solubility.: ethanol: 10 mg/mL
• Water Solubility.: Slightly soluble (hot)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 368.12598835
• Heavy Atom Count: 27
• Complexity: 507

Purity/Quality:

98% ^*data from raw suppliers

Curcumin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,F
• Statements: 36/37/38-11
• Safety Statements: 26-36-16-7-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)CC(=O)C=CC2=CC(=C(C=C2)O)OC)O
• Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C(=O)CC(=O)/C=C/C2=CC(=C(C=C2)O)OC)O
• Recent ClinicalTrials: Clinical Study of Curcumin in Preventing Postoperative Adhesion of Bilateral Vocal Cords
• Recent EU Clinical Trials: Efficacy of Hydroxychloroquine, Telmisartan and Azithromycin on Survival in Elderly Hospitalized Patients with VIDOC-19 : A Randomized, Multi-Centre, Adaptive, Blinded Study
• Recent NIPH Clinical Trials: Effects of consumption of the test food in healthy Japanese subjects with discomfort of knee and/or waist joints
• Description: Curcumin is the major yellow pigment in turmeric and curry and has antioxidant, anti-inflammatory, and antitumor activities. It inhibits nitric oxide (NO) production (IC50 = 6 μM) and reduces inducible nitric oxide synthase (iNOS) activity in LPS-stimulated RAW 264.7 cells. Curcumin inhibits release of histamine and the inflammatory cytokines TNF-α, IL-1β, IL-6, and IL-8 from HMC-1 mast cells. In vivo, curcumin decreases serum levels of histamine and TNF-α, inhibits histopathological changes of nasal mucosa, and decreases the number of sneezes and nasal rubbing in a mouse model of ovalbumin-induced rhinitis. Curcumin (100 or 200 mg/kg) prevents ovalbumin-induced accumulation of 3-nitrotyrosine (3-NT), a marker of oxidative stress, in mouse heart. Topical administration of curcumin (1-10 μmol) reduces the number of tumors induced by phorbol 12-myristate 13-acetate (TPA; ) in mouse skin. Dietary administration of curcumin reduces the number of tongue neoplasms and preneoplastic lesions induced by 4-nitroquinoline 1-oxide (4-NQO) in rats. The main source of curcumin is the root of Zingiberaceae Curcuma aromatica, rhizome of Curcuma longa (Jiang Huang), Curcuma zedoaria, and Acorus calamus. Among them, Jiang Huang contains about 3–6% curcumin. The traditional Chinese medicine, Jiang Huang, is the root tuber of perennial herbaceous plant Curcuma longa L. of family Zingiberaceae. It was firstly recorded in the “Tang materia medica” (Xin Xiu Ben Cao). It is pungent, bitter, and warm and enters the liver and spleen meridians. It activates the blood, moves qi, dredges meridians, and alleviates pain. In India and other Asian countries, Jiang Huang has more than 6000?years of application history. In Japan, Jiang Huang has a long history of health care, and the people of Okinawa Island regarded Jiang Huang as a holy tribute to the emperor. Jiang Huang mainly comes from Taiwan, Fujian, Guangdong, Guangxi, Yunnan, and Tibet of China and other regions in East Asia and Southeast Asia. It grows in warm and humid climate and sunny environment with abundant rainfall and fears cold frost, drought, and flood. At present, Chinese Pharmacopoeia only included Jiang Huang and Yu Jin which contains curcumin, while curcumin is not included.
• Physical properties: Appearance: orange-brown crystalline powder and tastes a little bitter. It will turn into reddish brown in alkaline solution and yellow in neutral and acidic solution. It has strong stability against the reducing agent. It has excellent pigmentation which is not easy to fade. It is sensitive to light, heat, and iron ion. When PH is greater than 8, curcumin turns from yellow to red, which can be used as a pH indicator.Solubility: insoluble in water or diethyl ether and soluble in ethanol, propylene glycol, acetic acid, and alkali solution.Melting point: about 183 °C.
• Uses: For preparing curcuma paper, pH range 8-9. In the detection of boron. A natural phenolic compound. Potent anti-tumor agent having anti-inflammatory and anti-oxidant properties. Induces apoptosis in cancer cells and inhibits phorbol ester-induced protein kinase C (PKC) activity. Reported to inhibit production of inflammatory cytokines by peripheral blood monocytes and alveolar macrophages. Potent inhibitor of EGFR tyrosine kinase and IκB kinase. Inhibits inducible nitric oxide synthase (iNOS), cycloxygenase and lipoxygenase. Easily penetrates into the cytoplasm of cells, accumulating in membranous structures such as plasma membrane, endoplasmic reticulum and nuclear envelope. antiedemic, antiinflammatory, bile stimulant; antibacterial, antifungal, lipo/cyclooxygenase inhibitor Curcumin is the principal curcuminoid of the popular Indian spice turmeric, which is a member of the ginger family (Zingiberaceae). The curcuminoids are polyphenols and are responsible for the yellow color of turmeric. Curcumin can exist in at least two t
• Clinical Use: 1. Cholagogic effect could promote bile formation and secretion. 2. Hypolipidemic effect could reduce the level of cholesterol in the blood and prevent atherosclerosis. 3. Antibacterial and antiviral effect could inhibit Staphylococcus aureus and HIV. 4. Liver protection. 5. Anticancer and antitumor effect. 6. Help with the prevention of dementia. 7. Anti-inflammation and treatment of acne and dermatitis. 8. There are no reports of adverse effect of curcumin till now.

Technology Process of Curcumin

There total 41 articles about Curcumin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

vanillin (121-33-5,8014-42-4) + acetylacetone (123-54-6,81235-32-7) → curcumin (458-37-7)

Guidance literature:

vanillin; acetylacetone; With boron trioxide; boric acid tributyl ester; In ethyl acetate; for 0.333333h;

With N-butylamine; In ethyl acetate; at 80 ℃; for 15h;

DOI:10.1021/jf902244g

Reference yield: 22.0%

vanillin (121-33-5,8014-42-4) + acetylacetone (123-54-6,81235-32-7) → curcumin (458-37-7) + 4-hydroxy-6-(4-hydroxy-3-methoxyphenyl)3,5-hexadien-2-one (1924-25-0)

Guidance literature:

With piperidine; triethyl borate; boron trioxide; In 1,4-dioxane;

DOI:10.1016/j.bmcl.2013.11.039

Reference yield:

1,7-bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,6-diene-3,5-dione; curcumin-tris hydrobromide → curcumin (458-37-7) + hydrogen bromide (10035-10-6,12258-64-9)

Guidance literature:

an trockner Luft;

upstream raw materials:

4-oxopentanal

vanillin

acetylacetone

(1ξ)-1-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-6-heptene-3,5-dione

Downstream raw materials:

1,7-bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,6-diene-3,5-dione; potassium-compound

curcumin

1,7-bis(4-hydroxy-3-methoxyphenyl)-heptane-3,5-dione

4',4'''-dinitro-4,4''-azo-bis-stilbene-2,2'-disulfonic acid ; tetrasodium-compound

Refernces

• 1、 Anjana,Joseph, Josna,John, Jeena,Balachandran,Kumar, T. R. Santhosh,Abraham, Annie. "Novel flourescent spiroborate esters: potential therapeutic agents in in vitro cancer models". . p. 727 - 740. Retrieved 2019.
• 2、 Pallikkavil, Radhika,Ummathur, Muhammed Basheer,Sreedharan, Sajith,Krishnankutty, Krishnannair. "Synthesis, characterization and antimicrobial studies of Cd(II), Hg(II), Pb(II), Sn(II) and Ca(II) complexes of curcumin". . p. 123 - 127. Retrieved 2013.
• 3、 Mitra, Koushambi,Gautam, Srishti,Kondaiah, Paturu,Chakravarty, Akhil R.. "Platinum(II) Complexes of Curcumin Showing Photocytotoxicity in Visible Light". . p. 1753 - 1763. Retrieved 2017.
• 4、 Wichitnithad, Wisut,Nimmannit, Ubonthip,Callery, Patrick S.,Rojsitthisak, Pornchai. "Effects of different carboxylic ester spacers on chemical stability, release characteristics, and anticancer activity of mono-PEGylated curcumin conjugates". . p. 5206 - 5218. Retrieved 2011.
• 5、 Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar. "Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites". supporting information. p. 1929 - 1940. Retrieved 2022/02/01.
• 6、 Rajasekharan, Kallikat Narayanan,Thomas, Sherin Geevarghese. "Extraction of curcumin from turmeric powder through complexation". . p. 695 - 699. Retrieved 2021/07/10.