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Curcumin(CAS No. 458-37-7)

Curcumin C21H20O6 (cas 458-37-7) Molecular Structure

458-37-7 Structure

Identification and Related Records

【Name】
Curcumin
【CAS Registry number】
458-37-7
【Synonyms】
1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxy-3-methoxyphenyl)-, (E,E)-
1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
diferuloylmethane
C.I. 75300
C.I. natural yellow 3
curouma
E-100
gelbwurz
Haidr
Halad
haldar
Halud
indian saffron
kachs haldi
merita earth
Natural Yellow 3
safra d'inde
souchet
terra merita
tumeric yellow
yellow ginger
yellow root
YO-KIN
【EINECS(EC#)】
207-280-5
【Molecular Formula】
C21H20O6 (Products with the same molecular formula)
【Molecular Weight】
368.38
【Inchi】
InChI=1/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+
【Canonical SMILES】
COC1=C(C=CC(=C1)C=CC(=O)CC(=O)C=CC2=CC(=C(C=C2)O)OC)O
【Isomers smiles】
COC1=C(C=CC(=C1)/C=C/C(=O)CC(=O)/C=C/C2=CC(=C(C=C2)O)OC)O
【MOL File】
458-37-7.mol

Chemical and Physical Properties

【Appearance】
orange crystalline powder
【Density】
0.93
【Melting Point】
183℃
【Boiling Point】
591.4 °C at 760 mmHg
【Vapour】
6.43E-15mmHg at 25°C
【Refractive Index】
1.4155-1.4175
【Flash Point】
208.9 °C
【Water】
Slightly soluble (hot)
【Solubilities】
Water solubility: Slightly soluble (hot)
【Color/Form】
orange
【Stability】
Stable, but may be light sensitive. Incompatible with strong oxidizing agents.
【HS Code】
29145000
【Storage temp】
20°C
【Spectral properties】
MAX ABSORPTION (DIOXANE): 265 NM (LOG E= 4.18); 420 NM (LOG E= 4.77)
IR: 13460 (Sadtler Research Laboratories Prism Collection)
UV: 6-924 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
【Computed Properties】
Molecular Weight:368.3799 [g/mol]
Molecular Formula:C21H20O6
XLogP3-AA:3.2
H-Bond Donor:2
H-Bond Acceptor:6
Rotatable Bond Count:8
Tautomer Count:51
Exact Mass:368.125988
MonoIsotopic Mass:368.125988
Topological Polar Surface Area:93.1
Heavy Atom Count:27
Formal Charge:0
Complexity:507
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:2
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:2
Feature 3D Anion Count:1
Feature 3D Ring Count:2
Effective Rotor Count:8
Conformer Sampling RMSD:1
CID Conformer Count:82

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/37/38
【Safety Statements 】
S26;S36
【Hazard Note】

Irritant

【Safety】

Moderately toxic by ingestion and intraperitoneal routes. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
The Hazard Codes of Curcumin (CAS NO.458-37-7): ?Xi
Hazard Note: Irritant
Risk Statements:
36/37/38:? Irritating to eyes, respiratory system and skin??
Safety Statements: ?
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36:? Wear suitable protective clothing?
WGK Germany: 2
RTECS: MI5230000

【Transport】
25kgs
【Formulations/Preparations】
DERIVATIVES: TINCTURE (20% IN 60% ETHANOL), FLUID EXTRACT, & OLEORESIN. /DERIV OF TURMERIC/
【Specification】

?Curcumin , its cas register number is 458-37-7. It also can be called 1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione ; C.I. Natural Yellow 3 ; Diferuloylmethane ; and C.I. 75300 . It is the principal curcuminoid of the popular Indian spice turmeric, and? can exist in at least two tautomeric forms, keto and enol.?Its biosynthetic route has proven to be very difficult for researchers to determine.?Curcumin can interfere with the activity of the transcription factor NF-κB, which has been linked to a number of inflammatory diseases such as cancer.

【Report】

Reported in EPA TSCA Inventory.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

OCCURS NATURALLY IN THE ROOT OF THE HERB CURCUMA LONGA (TURMERIC); ISOLATION BY STEAM DISTILLATION
ESSENTIAL OIL OF C LONGA...IS OBTAINED BY STEAM DISTILLATION, WITH YIELDS RANGING BETWEEN 1.3 & 5.5%. ... OIL CONTAINS, IN ADDITION TO TUMERONE, FREE ACIDS, CINEOL, BORNEOL, ZINGERONE, PHELLANDRENE, & 3-4% COLORING MATTER (CURCUMIN). /ESSENTIAL OIL OF CURCUMA LONGA/
STIEGLITZ, HORN, GERMAN PATENT 859,145 (1952 TO HOECHST).
U.S. Exports

(1977) ND
(1979) ND
U.S. Imports

(1977) 1.12X10+9 GRAMS AS TUMERIC
(1979) 1.54X10+9 GRAMS AS TUMERIC
U.S. Production

(1976) 6.4X10+8 G-MIN USE IN FOODS-AS TURMERIC
(1979) ND
【Usage】

For preparing curcuma paper, ph range 8-9, in detection of boron.

Biomedical Effects and Toxicity

【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 .
【Pharmacological Action】
- Anti-inflammatory agents that are not steroids. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They are used primarily in the treatment of chronic arthritic conditions and certain soft tissue disorders associated with pain and inflammation. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. Certain NSAIDs also may inhibit lipoxygenase enzymes or TYPE C PHOSPHOLIPASES or may modulate T-cell function. (AMA Drug Evaluations Annual, 1994, p 1814-5)
- Substances that inhibit or prevent the proliferation of NEOPLASMS.
- Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS.
- Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
【Therapeutic 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.
【Biomedical Effects and Toxicity】
ORAL & IP DOSES OF (3)H-CURCUMIN LED TO FECAL EXCRETION OF MOST OF RADIOACTIVITY. IV & IP DOSES WERE WELL EXCRETED IN BILE OF CANNULATED RATS.
WHEN ADMIN ORALLY IN DOSE OF 1 G/KG, CURCUMIN WAS EXCRETED IN FECES TO ABOUT 75%, WHILE NEGLIGIBLE AMT APPEARED IN URINE. MEASUREMENT OF BLOOD PLASMA LEVELS & BILIARY EXCRETION SHOWED THAT CURCUMIN WAS POORLY ABSORBED FROM THE GUT.

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