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458-37-7

Basic Information
CAS No.: 458-37-7
Name: 1,6-Heptadiene-3,5-dione,1,7-bis(4-hydroxy-3-methoxyphenyl)-, (1E,6E)-
Article Data: 60
Cas Database
Molecular Structure:
Molecular Structure of 458-37-7 (1,6-Heptadiene-3,5-dione,1,7-bis(4-hydroxy-3-methoxyphenyl)-, (1E,6E)-)
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: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information: N/A
PSA: 96.22000
LogP: 3.85260
Synthetic route
121-33-5

vanillin

123-54-6

acetylacetone

458-37-7

curcumin

Conditions
ConditionsYield
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%
121-33-5

vanillin

123-54-6

acetylacetone

A

458-37-7

curcumin

B

1924-25-0

4-hydroxy-6-(4-hydroxy-3-methoxyphenyl)3,5-hexadien-2-one

Conditions
ConditionsYield
With piperidine; triethyl borate; boron trioxide In 1,4-dioxaneA 8%
B 22%
626-96-0

4-oxopentanal

121-33-5

vanillin

A

458-37-7

curcumin

B

(1E,6E)-4-(4-hydroxy-3-methoxybenzylidene)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

Conditions
ConditionsYield
With boron trioxide
112494-43-6

(1ξ)-1-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-6-heptene-3,5-dione

458-37-7

curcumin

Conditions
ConditionsYield
at 130℃; under 15 Torr; for 10h;
123-08-0

4-hydroxy-benzaldehyde

121-33-5

vanillin

123-54-6

acetylacetone

A

458-37-7

curcumin

Conditions
ConditionsYield
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
123-08-0

4-hydroxy-benzaldehyde

123-54-6

acetylacetone

A

458-37-7

curcumin

Conditions
ConditionsYield
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
121-33-5

vanillin

123-54-6

acetylacetone

A

458-37-7

curcumin

Conditions
ConditionsYield
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

1,7-bis-(3-methoxy-4-methoxycarbonyloxy-phenyl)-hepta-1,6-diene-3,5-dione

67-64-1

acetone

KOH-solution

KOH-solution

458-37-7

curcumin

1,7-bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,6-diene-3,5-dione; curcumin-tris hydrobromide

A

458-37-7

curcumin

B

10035-10-6, 12258-64-9

hydrogen bromide

Conditions
ConditionsYield
an trockner Luft;

1,7-bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,6-diene-3,5-dione; curcumin-tris hydrobromide

A

458-37-7

curcumin

B

10035-10-6, 12258-64-9

hydrogen bromide

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

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.