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Curcumin

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Curcumin Basic information

Product Name:
Curcumin
CAS:
458-37-7
MF:
C21H20O6
MW:
368.38
EINECS:
207-280-5
Mol File:
458-37-7.mol
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Curcumin Chemical Properties

Melting point:
183 °C
Boiling point:
418.73°C (rough estimate)
Density 
0.93
vapor density 
13 (vs air)
refractive index 
1.4155-1.4175
Flash point:
14℃
storage temp. 
−20°C
solubility 
ethanol: 10 mg/mL
form 
powder
Colour Index 
75300
pka
8.09(at 25℃)
color 
orange
Odor
Odorless
PH Range
Yellow (7.8) to red-brown (9.2)
Water Solubility 
Slightly soluble (hot)
λmax
430nm
Merck 
14,2673
BRN 
2306965
Stability:
Stable, but may be light sensitive. Incompatible with strong oxidizing agents.
Major Application
Cosmetics, drug-eluting stents, inhibition of formation of skin-wrinkles, treating alzheimer’s disease, skin diseases, coronary restenosis, diabetes, obesity, leukemia, neurofibromas, cancer, antimicrobial, antiviral, antiinflammatory, antiprostate cancer
InChIKey
VFLDPWHFBUODDF-FCXRPNKRSA-N
CAS DataBase Reference
458-37-7(CAS DataBase Reference)
EPA Substance Registry System
Curcumin (458-37-7)
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Safety Information

Hazard Codes 
Xi,F
Risk Statements 
36/37/38-11
Safety Statements 
26-36-16-7-37/39
RIDADR 
UN1170 - class 3 - PG 2 - Ethanol, solution
WGK Germany 
2
RTECS 
MI5230000
Hazard Note 
Irritant
TSCA 
Yes
HazardClass 
3
PackingGroup 
II
HS Code 
29145000
Hazardous Substances Data
458-37-7(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: > 5000 mg/kg

MSDS

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Curcumin Usage And Synthesis

Chemical Properties

orange crystalline powder

Chemical Properties

Several species of Curcuma exist: C. xanthorrhyza, C. domestica, C. zedoafia, C. caesia and C. amada. Although all these are aromatic plants, C. longa is the one used as a flavor ingredient. The plant is originally from southern Asia and is widespread throughout India, Malaysia, Ceylon and Japan. It is a perennial herb whose rhizome yields (like that of ginger, which it also resembles) climbing stalks with leaves only or with leaves and flowers. Reproduction occurs through the splitting of the rhizome, which is the only part used (dried rhizome as is or after previously boiling in water). Turmeric has a spicy, fresh odor reminiscent of sweet orange and ginger and a slightly pungent, bitter flavor.

Uses

For preparing curcuma paper, pH range 8-9. In the detection of boron.

Uses

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.

Uses

antiedemic, antiinflammatory, bile stimulant; antibacterial, antifungal, lipo/cyclooxygenase inhibitor

Uses

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

Definition

ChEBI: A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.

General Description

Orange-yellow needles.

Air & Water Reactions

Slightly soluble in hot water .

Reactivity Profile

Curcumin is sensitive to light and changes in pH. Curcumin may react with oxidizing materials.

Biological Activity

Antitumor, anti-inflammatory and antioxidant agent. Downregulates expression of reactive-oxygen-generating enzymes (cyclooxygenase, lipoxygenase, iNOS), TNF α , IL-1, IL-6, PKC, EGFR, NF- κ B, I κ B kinase and more. Upregulates expression of PPAR γ , p53, Nrf2. Also displays antimicrobial, antidiabetic neuro- and cardioprotective properties in vivo .

Anticancer Research

It is a yellow-colored polyphenolic compound found in turmeric and used as a foodadditive. It has antitumor effects involved in mutagenesis, cell cycle regulation,apoptosis, oncogene expression, and metastasis. Thus it regulates the initiation,promotion, and progression of disease (Hosseini and Ghorbani 2015). Its mechanismof action is diversified and convoluted. 10 μM curcumin suppresses binding of theTPA response element (TRE) by c-Jun/activator protein-1 in NIH 3 T3 cells ofmouse fibroblasts. Both protein kinase C and ornithine decarboxylase are alsoinhibited by curcumin. Inhibition of cyclooxygenase and lipoxygenase leads tosuppression of arachidonic acid cascade (Murakami et al. 1996). Curcumin is animpressive blocker of the activation of NF-κB by inhibiting IκB kinase (IKK).Curcumin also downregulates cyclin D1, suppresses the cell growth, and inducesapoptosis in prostate, breast, acute myelogenous leukemia, and multiple myelomacancer cells. It may act against psoriasis by inhibition of phosphorylase kinaseenzyme (Aggarwal and Shishodia 2004). Curcumin downregulates the TNF-inducedNF-κB-regulated gene products involved in cellular proliferation (cyclin D1, COX-2,c-myc), antiapoptosis (IAP2, IAP1, Bcl-2, XIAP, Bcl-xL, TRAF1, Bf1–1/A1,Cflip), and metastasis (MMP-9, VEGF, ICAM-1). It also suppresses the activity ofIκBα kinase, κBα degradation, IκBα phosphorylation, p65 nuclear translocation,p65 phosphorylation, and p65 acetylation (Aggarwal et al. 2008). It upregulates the expression of p53, p16, p21, EGR1 (early growth response protein1), ERK(extracellular signal-regulated kinase), JNK(c-Jun-N-terminal kinase), ElK1, Bax,and caspase 3, caspase8, and caspase9 proteins and downregulates Bcl2, mTOR,p65, Bcl-xL, AKT, EGFR, cdc2, retinoblastoma protein (Prb), c-myc, and cyclin D1proteins (Singh et al. 2016b). It can dissociate raptor from mTOR and inhibit mTORcomplex1. The inhibition of the Akt/mTOR signaling results from thedephosphorylation dependent on the calyculin A-sensitive protein phosphatase.Further, it modulating effect on AP-1 in HT-29 human colon cancer cells was foundto be a dose-dependent increase of AP-1 luciferase activity (Ravindran et al. 2009).
Curcumin is a dynamic element of turmeric, an outstanding Indian zest that isobtained from the plant Curcuma longa dried roots. Curcumin hindered PDGFR-incitedproliferation of human hepatic myofibroblasts (Zheng and Chen 2006). Theactivated mechanism by curcumin in PDGF signaling is as follows: Curcumindecreases the level of tyrosine phosphorylation of PDGFR-β and EGF-R; repressesthe action of ERK, JNK, and PI3/AKT; reduces cell growth; and induces apoptosisdose-dependently (Kunnumakkara et al. 2008). Moreover, curcumin interferes withPDGF signaling via relieving its inhibitory effect on PPARγ gene expression toreduce the cell growth; it also promotes the expression of PPARγ genes (Zhou et al.2007).
This compound is a yellow pigment produced by plants, mostly by those in theginger family (Zingiberaceae). Curcumin has enormous potential in terms of cancerprevention and treatment, and numerous studies and reviews described it as a potentantioxidant and anti-inflammatory agent (Aggarwal et al. 2003; Agrawal and Mishra2010). It inhibits biochemical activity, restraining overexpression of some signallingpathways and regulating the expression of tumour suppression genes (Cre?uet al. 2012). Temu kunci, or galangal (Boesenbergia pandurata), is a rhizome generallyused in cooking that can also be prepared to treat diarrhoea and mouth ulcers.It has been proven non-toxic to human skin fibroblast cells and offers protectiveeffects against colon cancer (Kirana et al. 2007). Turmeric (Curcuma longa) andginger (Zingiber officinale) are two plants that contain an abundance of curcuminand which have been investigated for their therapeutic properties. One piece ofresearch, for example, showed that ethanolic extract of turmeric showed anti-melanomaactivity against malignant melanomas (Danciu et al. 2015).

Purification Methods

Crystallise curcumin from EtOH or acetic acid. [Beilstein 8 IV 3697.]

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CurcuminSupplierMore

Puripharm Co., Ltd. Gold
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0572-2745768-1;0572-2717806-
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sales@puripharm.com;yzm@puripharm.com
Shaanxi billion Kang Long biological technology co., LTD Gold
Tel:
17791478691
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997832940@qq.com
J & K SCIENTIFIC LTD.
Tel:
010-82848833- ;010-82848833-
Email:
jkinfo@jkchemical.com;market6@jkchemical.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel:
21-61259100-
Email:
sh@meryer.com
INTATRADE GmbH
Tel:
+49 3493/605464
Email:
sales@intatrade.de
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