C7727 Sigma-Aldrich


≥94% (curcuminoid content), ≥80% (Curcumin)

Synonym: (E,E)-1,7-bis(4-Hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, Diferuloylmethane, Diferulylmethane, Natural Yellow 3

  • CAS Number 458-37-7

  • Linear Formula [HOC6H3(OCH3)CH=CHCO]2CH2

  • Molecular Weight 368.38

  •  Colour Index Number 75300

  •  Beilstein/REAXYS Number 2306965

  •  EC Number 207-280-5

  •  MDL number MFCD00008365

  •  PubChem Substance ID 24892983

  •  NACRES NA.47



Related Categories Antioxidant, Cancer Research, Cell Biology, Cell Signaling and Neuroscience, Core Bioreagents,
Quality Level   200
vapor density   13 (vs air)
assay   ≥80% (Curcumin)
  ≥94% (curcuminoid content)
form   powder
mp   175 °C
solubility   ethanol: 1 mg/mL
  DMSO: >11 mg/mL
  0.5 M NaOH: soluble (then immediately diluted in PBS)
storage temp.   −20°C
SMILES string   COc1cc(\C=C\C(=O)CC(=O)\C=C\c2ccc(O)c(OC)c2)ccc1O
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+
Gene Information   human ... APP(351), CYP1A2(1544)


General description

Curcumin is a pigment present in Curcuma longa L (turmeric). Also called diferuloyl methane, it is a symmetric molecule with a seven carbon linker connecting two o-methoxy phenolic groups containing aromatic rings. Curcumin is synthesized by Pabon′s reaction using vanillin and acetyl acetone in the presence of boric oxide.


Curcumin has been used:
• as a supplement to evaluate its anti-carcinogenic and anti-apoptotic effect on cancer cells and cardiomyocytes
• to test its anti-inflammatory effect in human promyelocytic leukemia cell line, the HL-60
• to evaluate its attenuating effect on amyloidαβ pathology


500 mg in poly bottle

Biochem/physiol Actions

A natural phenolic compound. Potent anti-tumor agent having anti-inflammatory and anti-oxidant properties. Curcumin has been cited as a potential chemopreventive agent, in addition to its chemotherapeutic activity. 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.

Safety & Documentation

Safety Information

NONH for all modes of transport
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles


NF-κB and Inflammation

Chronic inflammation is an underlying factor in the development and progression of many of the chronic diseases of aging, such as arthritis, atherosclerosis, diabetes, and cancer. Oxidative cellular ...
BioFiles 2007, 2.4, 14.
Keywords: Acetylations, Adhesion, Angiogenesis, Apoptosis, Cancer, Carcinogens, Catalysis, Cell culture, Cell proliferation, Cell signaling, Cellular processes, Degradations, Diabetes, Diseases, Environmental, Gene expression, Glycosylations, High performance liquid chromatography, Inflammation, PAGE, Phosphorylations, Thin layer chromatography, Transcription, transformation

Traditional Medicinals and Cancer

Traditional Chinese Medicine (TCM) is a healing art that has been practiced for thousands of years. The practice of TCM is a holistic approach that includes the use of herbal preparations, acupunctur...
Lynn Stephenson, Product Specialist, and Chloe McClanahan, Product Manager
Biofiles Vol. 8, No. 6
Keywords: Analgesics, Antitumor agents, Apoptosis, Cancer, Drug discovery, Fractionation, High performance liquid chromatography, Metabolites, Metabolomics, Nuclear magnetic resonance spectroscopy, Pharmaceutical

Peer-Reviewed Papers


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