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| CAS No.: | 458-37-7 |
|---|---|
| Name: | Curcumin |
| Molecular Structure: | |
|
|
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| Formula: | C21H20O6 |
| Molecular Weight: | 368.386 |
| Synonyms: | 1,6-Heptadiene-3,5-dione,1,7-bis(4-hydroxy-3-methoxyphenyl)-, (E,E)- (8CI);Curcumin (6CI);(1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione;(E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione;(E,E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione;C Yellow 15;C.I. 75300;C.I. Natural Yellow 3;Curcuma;Curcumin I;Diferuloylmethane;E 100;E 100 (dye);Halud;IndianSaffron;Kacha Haldi;Merita Earth;NSC 32982;San-Ei Curcumine AL;San-Ei Gen Curcumine AL;Terra Merita;Turmeric;Turmeric yellow;Ukon (dye);Yellow Ginger;trans,trans-Curcumin;Curcumin; |
| EINECS: | 207-280-5 |
| Density: | 1.279 g/cm3 |
| Melting Point: | 183 °C |
| Boiling Point: | 591.4 °C at 760 mmHg |
| Flash Point: | 208.9 °C |
| Solubility: | slightly soluble in hot water |
| Appearance: | orange crystalline powder |
| Hazard Symbols: |
 Xi
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| Risk Codes: | 36/37/38 |
| Safety: | 26-36 |
| PSA: | 96.22000 |
| LogP: | 3.85260 |
| Conditions | Yield |
|---|---|
| Stage #1: vanillin; acetylacetone With boron trioxide; boric acid tributyl ester In ethyl acetate for 0.333333h; Stage #2: With N-butylamine In ethyl acetate at 80℃; for 15h; | 93% |
| Stage #1: vanillin; acetylacetone With boron trioxide; boric acid tributyl ester In ethyl acetate at 50℃; for 0.166667h; Stage #2: With N-butylamine In ethyl acetate at 50 - 80℃; for 4.25h; | 85% |
| Stage #1: vanillin; acetylacetone With boron trioxide; boric acid tributyl ester In ethyl acetate at 50℃; for 0.0833333h; Aldol condensation; Inert atmosphere; Stage #2: With N-butylamine In ethyl acetate at 50 - 80℃; for 4.25h; Inert atmosphere; Stage #3: With hydrogenchloride In water; ethyl acetate for 0.5h; Inert atmosphere; | 81% |
vanillin
acetylacetone
A
curcumin
B
4-hydroxy-6-(4-hydroxy-3-methoxyphenyl)3,5-hexadien-2-one
| Conditions | Yield |
|---|---|
| With piperidine; triethyl borate; boron trioxide In 1,4-dioxane | A 8% B 22% |
| Conditions | Yield |
|---|---|
| With boron trioxide |
(1ξ)-1-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-6-heptene-3,5-dione
curcumin
| Conditions | Yield |
|---|---|
| at 130℃; under 15 Torr; for 10h; |
4-hydroxy-benzaldehyde
vanillin
acetylacetone
A
curcumin
B
bisdemethoxycurcumin
C
demethoxycurcumin
| Conditions | Yield |
|---|---|
| With boric acid tributyl ester; boric acid In ethyl acetate at 40℃; for 0.5h; | A 2.1 g B 0.7 g C 2.6 g |
4-hydroxy-benzaldehyde
acetylacetone
A
curcumin
B
bisdemethoxycurcumin
C
demethoxycurcumin
| Conditions | Yield |
|---|---|
| With boric acid tributyl ester; boric acid; vanillin In ethyl acetate at 40℃; for 0.5h; | A 2.1 g B 0.7 g C 2.6 g |
vanillin
acetylacetone
A
curcumin
B
bisdemethoxycurcumin
C
demethoxycurcumin
| Conditions | Yield |
|---|---|
| With boric acid tributyl ester; boric acid; 4-hydroxy-benzaldehyde In ethyl acetate at 40℃; for 0.5h; | A 2.1 g B 0.7 g C 2.6 g |
A
curcumin
B
hydrogen bromide
| Conditions | Yield |
|---|---|
| an trockner Luft; |
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Reported in EPA TSCA Inventory.
The Curcumin, with the CAS registry number 458-37-7, is also known as 1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione; C.I. 75300; C.I. Natural Yellow 3; Diferuloylmethane. It belongs to the product categories of Colorants;Natural Plant Extract;Aromatics;Pharmaceuticals.This chemical's molecular formula is C21H20O6 and molecular weight is 368.38.Its EINECS number is 207-280-5. What's more,Its systematic name is Curcumin.It is orange crystalline powder,Stable,but may be light sensitive,Incompatible with strong oxidizing agents,Slightly soluble in hot water.Curcumin is sensitive to light and changes in pH,and may react with oxidizing materials.
Physical properties about Curcumin are:
(1)ACD/LogP: 3.071; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.07; (4)ACD/LogD (pH 7.4): 2.96; (5)ACD/BCF (pH 5.5): 126.55; (6)ACD/BCF (pH 7.4): 98.45; (7)ACD/KOC (pH 5.5): 1111.61; (8)ACD/KOC (pH 7.4): 864.84; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 10; (12)Index of Refraction: 1.643; (13)Molar Refractivity: 104.048 cm3 ; (14)Molar Volume: 287.893 cm3; (15)Surface Tension: 54.3230018615723 dyne/cm; (16)Density: 1.28 g/cm3; (17)Flash Point: 208.941 °C; (18)Enthalpy of Vaporization: 91.47 kJ/mol; (19)Boiling Point: 591.364 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.
Uses of Curcumin:
The Curcumin is brightly colored and may be used as a food coloring. It has been used historically as a component of Indian Ayurvedic medicine since 1900 BCE to treat a wide variety of ailments.It is obtained from tumeric, the powdered root of curcuma longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.It is 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.
You can still convert the following datas into molecular structure:
(1)SMILES:O=C(\C=C\c1ccc(O)c(OC)c1)CC(=O)\C=C\c2cc(OC)c(O)cc2;
(2)Std. InChI: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+;
(3)Std. InChIKey:VFLDPWHFBUODDF-FCXRPNKRSA-N;
The toxicity data of Curcumin as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 1500mg/kg (1500mg/kg) | Indian Journal of Medical Research. Vol. 64, Pg. 601, 1976. | |
| mouse | LD50 | oral | > 2gm/kg (2000mg/kg) | Journal of Pharmacy and Pharmacology. Vol. 25, Pg. 447, 1973. | |
| rat | LD | oral | > 2gm/kg (2000mg/kg) | Planta Medica. Vol. 64, Pg. 353, 1998. |
