Merck
All Photos(4)

Documents

C1386

Sigma-Aldrich

Curcumin

from Curcuma longa (Turmeric), powder

Sign Into View Organizational & Contract Pricing

Synonym(s):
(E,E)-1,7-bis(4-Hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, Diferuloylmethane, Diferulylmethane, Natural Yellow 3
Linear Formula:
[HOC6H3(OCH3)CH=CHCO]2CH2
CAS Number:
Molecular Weight:
368.38
Colour Index Number:
75300
Beilstein:
2306965
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

Curcuma longa (Turmeric)

vapor density

13 (vs air)

form

powder

concentration

≥65% (HPLC)

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.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

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+

InChI key

VFLDPWHFBUODDF-FCXRPNKRSA-N

Gene Information

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
PHR2209C772778246
Curcumin from Curcuma longa (Turmeric), powder

Sigma-Aldrich

C1386

Curcumin

Curcumin Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR2209

Curcumin

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

Sigma-Aldrich

C7727

Curcumin

Curcumin matrix substance for MALDI-MS, ≥99.5% (HPLC)

Supelco

78246

Curcumin

form

powder

form

solid

form

powder

form

powder

solubility

ethanol: 10 mg/mL, DMSO: >11 mg/mL (lit.)(lit.), 0.5 M NaOH: soluble (then immediately dilute in PBS [lit.])(lit.)

solubility

-

solubility

ethanol: 1 mg/mL, DMSO: >11 mg/mL, 0.5 M NaOH: soluble (then immediately diluted in PBS)

solubility

-

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

-

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

-

storage temp.

−20°C

storage temp.

-10 to -25°C

storage temp.

−20°C

storage temp.

2-8°C

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

100

General description

Curcumin is a yellow-colored polyphenol obtained from the rhizome of Curcuma longa L. It constitutes an important part of various diets and herbal medicines, especially in the Asian continent for its various salubrious effects on human health.

Application

Curcumin has been used:
  • to study its effect on the consequences and mechanism involved in the suppression of human homeobox gene NKX3.1 in the prostate cancer cell LNCaP
  • to examine its effect on stress in pigs by having an inhibitory impact on the serum cortisol concentration, hippocampal nitric oxide production, and brain-derived neurotrophic factor expression
  • to study its effect as a dietary supplement on the growth, immunity, antioxidant activity, and disease resistance in Oreochromis niloticus
  • to analyze its protective effect on the organotypic hippocampal slice cultures against the synaptic toxicity caused by amyloid beta peptides (Aβ1–42)
  • to examine the possibility of its non-toxic concentrations to decrease the inflammation caused by interleukin-1beta (IL-1β) in cartilage explant cultures
  • to study its protective impact against intestinal ischemia-reperfusion injury in rats
  • 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 its effects on Parkinson′s disease (PD)-like phenotypes

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 possesses anti-inflammatory, cancer prophylactic, and anti-oxidant properties. It also exhibits antagonistic nature towards the cluster of colon, breast, and blood marrow cancer. It does so by means of having an inhibitory effect on the various associated enzymes such as cycloxygenase-2 (COX-2), lipoxygenase and ornithine decarboxylase. It is also postulated to have anti-depressant, anti-stress and neuroprotective effects on humans and other animals. It is being proclaimed to be used as a treatment for Alzheimer′s disease due to its ability to cause synaptic toxicity. Additionally, it also shows anti-fungal, antiviral, anti-microbial, chemosensitizing, radiosensitizing, and wound healing activities.

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 sigma.com/discover-bsm.

related product

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 7

1 of 7

Bisdemethoxycurcumin ≥98% (HPLC), solid

Sigma-Aldrich

B6938

Bisdemethoxycurcumin

USP

USP

1151866

Curcuminoids

Piperine ≥97%

Sigma-Aldrich

P49007

Piperine

Demethoxycurcumin analytical standard

Supelco

90593

Demethoxycurcumin

Tetrahydrocurcumin analytical standard

Supelco

50202

Tetrahydrocurcumin

Bisdemethoxycurcumin analytical standard

Supelco

90594

Bisdemethoxycurcumin

Tetrahydrocurcumin ≥96% (HPLC)

Sigma-Aldrich

SMB00370

Tetrahydrocurcumin

In vitro inhibitory effects of Andrographis paniculata, Gynura procumbens, Ficus deltoidea, and Curcuma xanthorrhiza extracts and constituents on human liver glucuronidation activity
Husni Z, et al.
Pharmacognosy magazine, 13(Suppl 2), S236-S236 (2017)
Assessment of diets containing curcumin, epigallocatechin-3-gallate, docosahexaenoic acid and alpha-lipoic acid on amyloid load and inflammation in a male transgenic mouse model of Alzheimer's disease: Are combinations more effective?
Sharman MJ, et al.
Neurobiology of Disease, 124, 505-519 (2019)
Curcumin's biphasic hormetic response on proteasome activity and heat-shock protein synthesis in human keratinocytes
Ali RE and Rattan SIS
Annals of the New York Academy of Sciences, 1067(1), 394-399 (2006)
Dietary curcumin supplement influence on growth, immunity, antioxidant status, and resistance to Aeromonas hydrophila in Oreochromis niloticus
Mahmoud HK, et al.
Aquaculture (Amsterdam, Netherlands), 475, 16-23 (2017)
Curcumin effectively rescued Parkinson?s disease-like phenotypes in a novel drosophila melanogaster model with dUCH Knockdown
Nguyen TT, et al.
Oxidative Medicine and Cellular Longevity, 2018 (2018)

Articles

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Related Content

DISCOVER Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service