C1386 Sigma-Aldrich


from Curcuma longa (Turmeric), powder

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 24892408

  •  NACRES NA.77



Related Categories Antioxidant, Application Index, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Bioactive Small Molecules for Epigenetic Research,
Quality Level   200
biological source   Curcuma longa (Turmeric)
vapor density   13 (vs air)
assay   ≥65% (HPLC)
form   powder
mp   175  °C
solubility   ethanol: 10 mg/mL
  DMSO: >11 mg/mL (lit.)(lit.)
  0.5 M NaOH: soluble (then immediately dilute in PBS [lit.])(lit.)
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)



Curcumin has been used:
• to measure its antibacterial activity in vitro
• to determine its preventative effects for Alzheimer′s disease (AD) in mice
• as a bifunctional agent for generation and validation of the erythroid 2-related factor 2 (Nrf2) reporter system
• to study its in vitro inhibitory effects on human liver glucuronidation activity
• to evaluate the effects of curcumin on Parkinson′s disease (PD)-like phenotypes


5, 10, 50 g in glass 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.

Curcumin (diferuloylmethane) is a constituent of the yellow powder extracted from the roots of Curcuma longa Linn, also known as tumeric or turmeric. It is used as a spice and coloring agent for centuries. In addition, it is used to treat various diseases including, hepatic disorders, anorexia, diabetic wounds and rheumatism.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at

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


Balancing Histone/Protein Acetylation: Gene Regulation and Cancer Therapy

A highly sophisticated mechanism organizes the 2-meter long human genome within a 6-μm wide nucleus. Up to 10,000-fold of compaction of the chromatin is achieved during mitosis, allowing faithful seg...
Min-Hao Kuo
LSI Volume 7 Article 1
Keywords: Acetylations, Anaerobic, Apoptosis, Biochemistry, Cancer, Catalysis, Cell division, Cell proliferation, Chromatin immunoprecipitation, Clinical, DNA replication, Degradations, Environmental, Enzymology, Gene expression, Genetic, Genetics, Hormones, Immunoprecipitation, Indicators, Mass spectrometry, Metal organic frameworks, Methylations, Microarray Analysis, Molecular biology, Phase transitions, Phosphorylations, Recombination, Substitutions, Transcription

Discover Bioactive Small Molecules for Gene Regulation

The loss of regulation of gene expression is a key component to many human disease states, including neurodegenerative disorders, autoimmune conditions and, most prominently, cancers. Regulation of g...
Keywords: Acetylations, Epigenetics, Gene expression, Genomics, Methylations, PAGE, Post translational modifications, Transcription

Discover Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Exposure to harsh conditions, cellular damage, and other factors can cause stress on cells. Stress attributed directly and indirectly to oxygen is referred to as oxidative stress, which is imposed on...
Keywords: Antimicrobials, Bioactive small molecules, Cancer, Diseases, Neurodegenerative Diseases, Oxidations

Histone Modification and Chromatin Remodeling

Gene expression is governed by complex mechanisms including transcription factor binding to DNA and coordinated changes in chromatin structure. The primary protein components of chromatin are the his...
Savita Bagga, PhD.
BioFiles v7 n3, 2012, 10–16
Keywords: Acetylations, Amplification, Cancer, Cell culture, Chromatin immunoprecipitation, Cloning, DNA purification, Diseases, Epigenetics, Gene expression, Immunoprecipitation, Indicators, Methylations, Microarray Analysis, Polymerase chain reaction, Polymerase chain reaction - quantitative, Polymorphisms, Purification, Sequencing, Transcription, Whole genome amplification

The Role of Inflammation in Neurodegeneration

It is well established that the brain can sense and react to peripheral insults through the rapid induction of fever and other neuroendocrine changes in response to events such as infection and tissu...
Scott Hauser, Technology Transfer Specialist, Sigma® Life Science
Biofiles, Vol. 8, No. 19
Keywords: Adhesion, Central Nervous System, Diseases, Gene expression, Inflammation, Neurodegenerative Diseases, Reductions

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The biochemicals you use in your experiments directly impact the quality and reproducibility of your results. Biochemicals from us are world class products, competitively priced, and backed by superi...
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