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458-37-7

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458-37-7 Usage

Food Additive

Curcumin has been widely used in the food industry as a common natural pigment for a long time. It is mainly used for the dyeing of canned food, sausage products and soy sauce products. The amount of curcumin used is determined by normal production needs. The product form of functional food with curcumin as the main component can be general food or some non-food forms, such as capsules, pills or tablets. For general food form, some yellow pigmented foods can be considered, such as cakes, sweets, beverages, etc. Curcumin is a food additive approved by the Codex Alimentarius Commission of the Food and Agriculture Organization of the United Nations (FAO/WHO-1995). The newly promulgated "Standards for the Use of Food Additives" (GB2760-2011) stipulates that frozen drinks, cocoa products, chocolate and chocolate products and candies, gum-based candies, decorative candies, toppings and sweet sauces, batter, coating powder and frying powder , The maximum usage of curcumin in instant rice and noodle products, flavored syrup, compound seasoning, carbonated drinks and jelly is 0.15, 0.01, 0.7, 0.5, 0.3, 0.5, 0.5, 0.1, 0.01, 0.01 g/kg, respectively, margarine and its similar products, cooked nuts and seeds, fillings for grain products and puffed foods can be used in moderation according to production needs.

Description

Different sources of media describe the Description of 458-37-7 differently. You can refer to the following data:
1. Curcumin is the major yellow pigment in turmeric and curry and has antioxidant, anti-inflammatory, and antitumor activities. It inhibits nitric oxide (NO) production (IC50 = 6 μM) and reduces inducible nitric oxide synthase (iNOS) activity in LPS-stimulated RAW 264.7 cells. Curcumin inhibits release of histamine and the inflammatory cytokines TNF-α, IL-1β, IL-6, and IL-8 from HMC-1 mast cells. In vivo, curcumin decreases serum levels of histamine and TNF-α, inhibits histopathological changes of nasal mucosa, and decreases the number of sneezes and nasal rubbing in a mouse model of ovalbumin-induced rhinitis. Curcumin (100 or 200 mg/kg) prevents ovalbumin-induced accumulation of 3-nitrotyrosine (3-NT), a marker of oxidative stress, in mouse heart. Topical administration of curcumin (1-10 μmol) reduces the number of tumors induced by phorbol 12-myristate 13-acetate (TPA; ) in mouse skin. Dietary administration of curcumin reduces the number of tongue neoplasms and preneoplastic lesions induced by 4-nitroquinoline 1-oxide (4-NQO) in rats.
2. The main source of curcumin is the root of Zingiberaceae Curcuma aromatica, rhizome of Curcuma longa (Jiang Huang), Curcuma zedoaria, and Acorus calamus. Among them, Jiang Huang contains about 3–6% curcumin. The traditional Chinese medicine, Jiang Huang, is the root tuber of perennial herbaceous plant Curcuma longa L. of family Zingiberaceae. It was firstly recorded in the “Tang materia medica” (Xin Xiu Ben Cao). It is pungent, bitter, and warm and enters the liver and spleen meridians. It activates the blood, moves qi, dredges meridians, and alleviates pain. In India and other Asian countries, Jiang Huang has more than 6000?years of application history. In Japan, Jiang Huang has a long history of health care, and the people of Okinawa Island regarded Jiang Huang as a holy tribute to the emperor. Jiang Huang mainly comes from Taiwan, Fujian, Guangdong, Guangxi, Yunnan, and Tibet of China and other regions in East Asia and Southeast Asia. It grows in warm and humid climate and sunny environment with abundant rainfall and fears cold frost, drought, and flood. At present, Chinese Pharmacopoeia only included Jiang Huang and Yu Jin which contains curcumin, while curcumin is not included.

Chemical Properties

Different sources of media describe the Chemical Properties of 458-37-7 differently. You can refer to the following data:
1. 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.
2. orange crystalline powder

Physical properties

Appearance: orange-brown crystalline powder and tastes a little bitter. It will turn into reddish brown in alkaline solution and yellow in neutral and acidic solution. It has strong stability against the reducing agent. It has excellent pigmentation which is not easy to fade. It is sensitive to light, heat, and iron ion. When PH is greater than 8, curcumin turns from yellow to red, which can be used as a pH indicator.Solubility: insoluble in water or diethyl ether and soluble in ethanol, propylene glycol, acetic acid, and alkali solution.Melting point: about 183 °C.

History

Curcumin is one such agent that was described about two centuries ago as the yellow coloring matter from the rhizomes of Curcuma longa. Besides curcumin, more than 300 different components, including phenolics and terpenoids, have been identified in turmeric, but curcumin is one of the most important active components . Pure curcumin was prepared in 1842 by Vogel Jr. After 1870, the possible structure of curcumin was reported by several chemists in the subsequent decades. The chemical structure of curcumin as diferuloylmethane or 1,6-heptadiene-3,5-dione-1,7-bis (4-hydroxy-3-methoxyphenyl)-(1E, 6E) was reported by Milobedzka et?al. (1910). Lampe and Milobedzka (1913) reported the synthesis of curcumin. However, Srinivasan (1953) for the first time used chromatography to separate and quantify the components of curcumin .Jiang Huang has been used for more than 6000 years; it is also well known for its medicinal value and active ingredients. But it was not until the middle of the twentieth century that scientists conducted a systematic study on their pharmacological effects. In 1949, Schraufstatter and Bernt found that curcumin has a variety of antibacterial effects against Streptococcus, Salmonella, Mucor, Mycobacterium and so on . In the 1970s, the study also found that it has lipid-lowering, anti-inflammatory, antioxidant, and antidiabetic effects. In 1980s, it was found to have antitumor effects. In the last 30 years, there are many reports about the clinical and pharmacological effects of curcumin.At present, more than 65 human clinical trials have been completed, and more than 35 clinical trials are in progress. In addition, the study of curcumin derivatives has also become a hot topic in recent years.

Uses

Different sources of media describe the Uses of 458-37-7 differently. You can refer to the following data:
1. For preparing curcuma paper, pH range 8-9. In the detection of boron.
2. 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.
3. antiedemic, antiinflammatory, bile stimulant; antibacterial, antifungal, lipo/cyclooxygenase inhibitor
4. 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 .

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.

Mechanism of action

Curcumin, the active component of turmeric (Curcuma longa), has been regarded as an anti-inflammatory and antioxidant agent . Particularly, it can scavenge reactive oxygen species, such as hydroxyl radicals, superoxide anion radicals, and nitrogen dioxide radicals. Additionally, it serves as an anti-inflammatory by down-regulating the production of pro-inflammatory cytokines (e.g., IL-1 and TNF-α) and inhibiting the activation of specific transcription factors (e.g., NF-κB and AP-1). Curcumin also demonstrates antiproliferative properties. Specifically, it inhibits UV radiation-induced skin cancer in SKH-1 hairless mice and reduces UVB-induced matrix metalloproteinase-1/3 expression in human dermal fibroblasts via MAPK-p38/JNK pathway suppression.

Pharmacology

1. Anti-fibrosis effects: curcumin has the effect of anti-fibrosis in the lung, liver, kidney, and so on. It could inhibit the release of various inflammatory factors and reduce the expression of collagen, laminin, hyaluronic acid, and other extracellular matrix content. It could also reduce the transforming growth factors such as TGF-尾 to inhibit cell proliferation .2. Antitumor effects: the antitumor effect of curcumin is currently the most studied pharmacological effects and attracts a lot of attention worldwide. Curcumin has been proved to inhibit the proliferation of a variety of tumor cells through regulating a variety of transcription factors (NF-κB, AP-1, etc.), mitogen-activated protein kinase (MAPK), growth factor receptor kinase (PDGFR, VEGFR, etc.), and cyclooxygenase. It plays an important role in the cell cycle and further to inhibit proliferation. Curcumin can also inhibit the migration of tumor cells by activating caspase and inducing tumor cell apoptosis .3. Anti-inflammatory effects: curcumin has a strong inhibitory effect on different kinds of inflammation. The mechanism might relate to the reduction of the expression of prostaglandins and leukotriene to decrease the release of various inflammatory factors. The anti-inflammatory effect of curcumin is close to that of nonsteroidal anti-inflammatory drugs and glucocorticoids, but it has higher safety and lower side effects .4. Antimicrobial effects: curcumin has a strong inhibitory effect on bacteria, viruses, fungi, and parasites . Researchers believe that curcumin may play a role in inhibiting microbial survival and reproduction by destroying microbial cell membranes, inducing their genetic changes, and so on.5. Hypolipidemic effect: many researchers believe that curcumin will become a hypolipidemic drug with a good prospect. It can lower the levels of total blood cholesterol and triglyceride levels, increase apolipoprotein A level, promote lowdensity lipoprotein (LDL) metabolism, and increase LDL excretion to reduce LDL body content .6. Drug metabolism: rats were treated with a single dose of refined curcumin orally, 60–65% of which was absorbed by the gastrointestinal tract. Within 5 days, 40% of curcumin were excreted from the feces. The plasma concentration reached the peak after 3 days. The transformation of curcumin happened in the process of hepato-enteral circulation .

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).

Clinical Use

1. Cholagogic effect could promote bile formation and secretion. 2. Hypolipidemic effect could reduce the level of cholesterol in the blood and prevent atherosclerosis. 3. Antibacterial and antiviral effect could inhibit Staphylococcus aureus and HIV. 4. Liver protection. 5. Anticancer and antitumor effect. 6. Help with the prevention of dementia. 7. Anti-inflammation and treatment of acne and dermatitis. 8. There are no reports of adverse effect of curcumin till now.

Purification Methods

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

References

1) Zhang?et al.?(2015),?Anti-inflammatory effect of curcumin on mast cell-mediated allergic responses in ovalbumin-induced allergic rhinitis mouse; Cell Immunol.?298?88 2) Li?et al.?(2018),?Anticancer effects of curcumin on nude mice bearing lung cancer A549 cell subsets SP and NSP cells; Oncol. Lett.?16?6756

Check Digit Verification of cas no

The CAS Registry Mumber 458-37-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,5 and 8 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 458-37:
(5*4)+(4*5)+(3*8)+(2*3)+(1*7)=77
77 % 10 = 7
So 458-37-7 is a valid CAS Registry Number.
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/h3-13,22,24-25H,1-2H3/b7-3+,8-4+,16-13-

458-37-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (C0434)  Curcumin (Natural)  

  • 458-37-7

  • 1g

  • 155.00CNY

  • Detail
  • TCI America

  • (C0434)  Curcumin (Natural)  

  • 458-37-7

  • 25g

  • 685.00CNY

  • Detail
  • TCI America

  • (C2302)  Curcumin (Synthetic)  >97.0%(T)

  • 458-37-7

  • 5g

  • 395.00CNY

  • Detail
  • TCI America

  • (C2302)  Curcumin (Synthetic)  >97.0%(T)

  • 458-37-7

  • 25g

  • 1,250.00CNY

  • Detail
  • Alfa Aesar

  • (B21573)  Curcumin, 95% (total curcuminoid content), from Turmeric rhizome   

  • 458-37-7

  • 10g

  • 502.0CNY

  • Detail
  • Alfa Aesar

  • (B21573)  Curcumin, 95% (total curcuminoid content), from Turmeric rhizome   

  • 458-37-7

  • 50g

  • 1188.0CNY

  • Detail
  • Alfa Aesar

  • (B21573)  Curcumin, 95% (total curcuminoid content), from Turmeric rhizome   

  • 458-37-7

  • 250g

  • 4974.0CNY

  • Detail
  • Sigma-Aldrich

  • (28982)  Curcuminsolution  ~0.1 % (w/v) (in ethanol with 2M HCl (99:1 v/v)), for TLC derivatization

  • 458-37-7

  • 28982-100ML

  • 900.90CNY

  • Detail
  • Sigma-Aldrich

  • (08511)  Curcumin  analytical standard

  • 458-37-7

  • 08511-10MG

  • 360.36CNY

  • Detail
  • Sigma-Aldrich

  • (00280590)  Curcumin  primary pharmaceutical reference standard

  • 458-37-7

  • 00280590-10MG

  • 2,552.94CNY

  • Detail
  • USP

  • (1151855)  Curcumin  United States Pharmacopeia (USP) Reference Standard

  • 458-37-7

  • 1151855-30MG

  • 4,662.45CNY

  • Detail
  • Sigma

  • (C1386)  Curcumin  from Curcuma longa (Turmeric), powder

  • 458-37-7

  • C1386-5G

  • 477.36CNY

  • Detail

458-37-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name curcumin

1.2 Other means of identification

Product number -
Other names 1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxy-3-methoxyphenyl)-, (E,E)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:458-37-7 SDS

458-37-7Synthetic route

vanillin
121-33-5

vanillin

acetylacetone
123-54-6

acetylacetone

curcumin
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%
vanillin
121-33-5

vanillin

acetylacetone
123-54-6

acetylacetone

A

curcumin
458-37-7

curcumin

B

4-hydroxy-6-(4-hydroxy-3-methoxyphenyl)3,5-hexadien-2-one
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%
4-oxopentanal
626-96-0

4-oxopentanal

vanillin
121-33-5

vanillin

A

curcumin
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

(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
(1ξ)-1-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-6-heptene-3,5-dione
112494-43-6

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

curcumin
458-37-7

curcumin

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

4-hydroxy-benzaldehyde

vanillin
121-33-5

vanillin

acetylacetone
123-54-6

acetylacetone

A

curcumin
458-37-7

curcumin

B

bisdemethoxycurcumin
22608-12-4, 24939-16-0, 33171-05-0

bisdemethoxycurcumin

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
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

acetylacetone
123-54-6

acetylacetone

A

curcumin
458-37-7

curcumin

B

bisdemethoxycurcumin
22608-12-4, 24939-16-0, 33171-05-0

bisdemethoxycurcumin

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
vanillin
121-33-5

vanillin

acetylacetone
123-54-6

acetylacetone

A

curcumin
458-37-7

curcumin

B

bisdemethoxycurcumin
22608-12-4, 24939-16-0, 33171-05-0

bisdemethoxycurcumin

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

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

acetone
67-64-1

acetone

KOH-solution

KOH-solution

curcumin
458-37-7

curcumin

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

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

A

curcumin
458-37-7

curcumin

B

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

Conditions
ConditionsYield
an trockner Luft;
water
7732-18-5

water

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

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

A

curcumin
458-37-7

curcumin

B

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

curcumin phenoxyl radical

curcumin phenoxyl radical

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
With ascorbic acid In water; dimethyl sulfoxide Kinetics;
curcumin radical cation

curcumin radical cation

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
With triethylamine In various solvent(s) at 20℃; Kinetics;
vanillin
121-33-5

vanillin

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
Stage #1: acetylacetone With boron trioxide In ethyl acetate at 20℃; for 1h;
Stage #2: vanillin With boric acid tributyl ester for 1h;
Stage #3: With N-butylamine In ethyl acetate for 48h;
benzaldehyde
100-52-7

benzaldehyde

acetylacetone
123-54-6

acetylacetone

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
With boron trioxide
vanillin
121-33-5

vanillin

acetylacetone-boric oxide complex

acetylacetone-boric oxide complex

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
With tri-sec-butylborate; N-butylamine In ethyl acetate
4-hydroxy-3-(hydroxymethyl)benzaldehyde
54030-32-9

4-hydroxy-3-(hydroxymethyl)benzaldehyde

acetylacetone
123-54-6

acetylacetone

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
Stage #1: 4-hydroxy-3-(hydroxymethyl)benzaldehyde; acetylacetone With boron trioxide; 1,2,3,4-tetrahydroisoquinoline In acetic acid at 110℃; for 24h;
Stage #2: In water; acetic acid at 20℃; for 24h;
S-(hydrogen malonyl)coenzyme A
524-14-1

S-(hydrogen malonyl)coenzyme A

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
With fusion protein of diketide-CoA synthase and curcumin synthase In aq. phosphate buffer at 37℃; for 8h; pH=7.5; Enzymatic reaction;
S-(hydrogen malonyl)coenzyme A
524-14-1

S-(hydrogen malonyl)coenzyme A

A

(E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one
1080-12-2, 22214-42-2

(E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one

B

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
With curcumin synthase; diketide-CoA synthase In aq. phosphate buffer at 37℃; for 8h; pH=7.5; Enzymatic reaction;
C21H19O6(1-)

C21H19O6(1-)

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N,N-dimethyl-formamide / 12 h / 20 °C / Darkness
1.2: 5 h / 20 °C / Inert atmosphere; Darkness
2.1: dimethyl sulfoxide; water / 1 h / pH 7.2 / Irradiation
View Scheme
C21H25N2O6Pt(1+)*NO3(1-)

C21H25N2O6Pt(1+)*NO3(1-)

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
In water; dimethyl sulfoxide for 1h; pH=7.2; Irradiation;
C23H27N2O6Pt(1+)*NO3(1-)

C23H27N2O6Pt(1+)*NO3(1-)

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
In water; dimethyl sulfoxide for 1h; pH=7.2; Irradiation;
C27H33N2O6Pt(1+)*NO3(1-)

C27H33N2O6Pt(1+)*NO3(1-)

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
In water; dimethyl sulfoxide for 1h; pH=7.2; Irradiation;
rubrocurcumin

rubrocurcumin

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
With water In acetone at 50℃; Kinetics;
C24H21BO10

C24H21BO10

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
With water In acetone at 50℃; Kinetics;
C28H23BO9

C28H23BO9

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
With water In acetone at 50℃; Kinetics;
C27H25BO13

C27H25BO13

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
With water In acetone at 50℃; Kinetics;
rosacyanine

rosacyanine

curcumin
458-37-7

curcumin

Conditions
ConditionsYield
With ethanol In N,N-dimethyl acetamide Solvent;
curcumin
458-37-7

curcumin

acetic anhydride
108-24-7

acetic anhydride

1,7-bis(4-acetoxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
297179-80-7

1,7-bis(4-acetoxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione

Conditions
ConditionsYield
With pyridine In 2-methyltetrahydrofuran for 2h; Reflux;98%
With sodium acetate
With pyridine In dichloromethane for 2h; Reflux;
curcumin
458-37-7

curcumin

acetic anhydride
108-24-7

acetic anhydride

((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene)diacetate
19697-86-0

((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene)diacetate

Conditions
ConditionsYield
With pyridine In dichloromethane for 2h; Reflux;98%
With sodium hydrogencarbonate; sodium carbonate; potassium hydrogencarbonate; acetyl chloride In dichloromethane; toluene; acetonitrile at 0℃; for 20h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;96%
With pyridine In dichloromethane for 1h; Reflux;95%
curcumin
458-37-7

curcumin

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

urea
57-13-6

urea

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With phosphomolybdic acid In ethanol for 0.0583333h; Microwave irradiation; Green chemistry;98%
With piperidine In methanol at 60 - 65℃; for 20h;72%
curcumin
458-37-7

curcumin

thiourea
17356-08-0

thiourea

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(3,4-dihydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-thione

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(3,4-dihydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-thione

Conditions
ConditionsYield
With phosphomolybdic acid In ethanol for 0.0416667h; Microwave irradiation; Green chemistry;98%
curcumin
458-37-7

curcumin

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

4,4'-((1E,1'E)-(3H-benzo[b]-[1,4]-diazepine-2,4-diyl)bis(ethene-2,1-diyl))bis-(2-methoxyphenol)

4,4'-((1E,1'E)-(3H-benzo[b]-[1,4]-diazepine-2,4-diyl)bis(ethene-2,1-diyl))bis-(2-methoxyphenol)

Conditions
ConditionsYield
With sulfuric acid In ethanol at 20℃;97.5%
curcumin
458-37-7

curcumin

benzaldehyde
100-52-7

benzaldehyde

urea
57-13-6

urea

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
1373886-08-8

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-phenyl-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With tin(II) chloride dihdyrate at 80℃; for 1.33333h; Neat (no solvent);97%
With chitosan (viscosity 800–2000 cps) In water; acetic acid at 60℃; for 1.33333h; Green chemistry;97%
With phosphomolybdic acid In ethanol for 0.0416667h; Microwave irradiation; Green chemistry;97%
With piperidine In methanol at 60 - 65℃; for 16h;76%
curcumin
458-37-7

curcumin

salicylaldehyde
90-02-8

salicylaldehyde

urea
57-13-6

urea

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(2-hydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-one
1373886-13-5

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(2-hydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With phosphomolybdic acid In ethanol for 0.0416667h; Microwave irradiation; Green chemistry;97%
With tin(II) chloride dihdyrate at 80℃; for 1.5h; Neat (no solvent);96%
With piperidine In methanol at 60 - 65℃; for 18h;75%
curcumin
458-37-7

curcumin

thiourea
17356-08-0

thiourea

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-N,N-dimethylphenyl)-3,4-dihydropyrimidin-2(1H)-thione

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-N,N-dimethylphenyl)-3,4-dihydropyrimidin-2(1H)-thione

Conditions
ConditionsYield
With phosphomolybdic acid In ethanol for 0.0416667h; Microwave irradiation; Green chemistry;97%
With piperidine In methanol at 60 - 65℃; for 16h;80%
curcumin
458-37-7

curcumin

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

thiourea
17356-08-0

thiourea

5-(4-hydroxy-3-methoxyphenylethylene carbonyl)-6-(4-hydroxy,3-methoxyphenylethylene)-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-thione

5-(4-hydroxy-3-methoxyphenylethylene carbonyl)-6-(4-hydroxy,3-methoxyphenylethylene)-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-thione

Conditions
ConditionsYield
With phosphomolybdic acid In ethanol for 0.0416667h; Microwave irradiation; Green chemistry;97%
curcumin
458-37-7

curcumin

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

4,4'-((1E,1'E)-(7-chloro-3H-benzo[b]-[1,4]-diazepine-2,4-diyl)bis(ethene-2,1-diyl))bis-(2-methoxyphenol)

4,4'-((1E,1'E)-(7-chloro-3H-benzo[b]-[1,4]-diazepine-2,4-diyl)bis(ethene-2,1-diyl))bis-(2-methoxyphenol)

Conditions
ConditionsYield
With sulfuric acid In ethanol at 20℃;96.1%
curcumin
458-37-7

curcumin

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

thiourea
17356-08-0

thiourea

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-chlorophenyl)-3,4-dihydropyrimidin-2(1H)-thione
1373886-17-9

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-chlorophenyl)-3,4-dihydropyrimidin-2(1H)-thione

Conditions
ConditionsYield
With tin(II) chloride dihdyrate at 80℃; for 1.33333h; Neat (no solvent);96%
With phosphomolybdic acid In ethanol for 0.0416667h; Microwave irradiation; Green chemistry;96%
curcumin
458-37-7

curcumin

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

urea
57-13-6

urea

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-chlorophenyl)-3,4-dihydropyrimidin-2(1H)-one
1373886-09-9

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-chlorophenyl)-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With phosphomolybdic acid In ethanol for 0.0416667h; Microwave irradiation; Green chemistry;96%
With chitosan (viscosity 800–2000 cps) In water; acetic acid at 60℃; for 1.5h; Green chemistry;95%
With tin(II) chloride dihdyrate at 80℃; for 1.33333h; Neat (no solvent);94%
curcumin
458-37-7

curcumin

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

urea
57-13-6

urea

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one
1373886-10-2

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With tin(II) chloride dihdyrate at 80℃; for 1.5h; Neat (no solvent);96%
With chitosan (viscosity 800–2000 cps) In water; acetic acid at 60℃; for 1.33333h; Green chemistry;95%
curcumin
458-37-7

curcumin

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

urea
57-13-6

urea

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-hydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-one
1373886-14-6

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-hydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With chitosan (viscosity 800–2000 cps) In water; acetic acid at 60℃; for 1.33333h; Green chemistry;96%
With phosphomolybdic acid In ethanol for 0.0416667h; Microwave irradiation; Green chemistry;96%
With tin(II) chloride dihdyrate at 80℃; for 1.5h; Neat (no solvent);95%
With piperidine In methanol at 60 - 65℃; for 18h;62%
curcumin
458-37-7

curcumin

vanillin
121-33-5

vanillin

thiourea
17356-08-0

thiourea

C30H28N2O7S
1373886-20-4

C30H28N2O7S

Conditions
ConditionsYield
With chitosan (viscosity 800–2000 cps) In water; acetic acid at 60℃; for 1.33333h; Green chemistry;96%
With tin(II) chloride dihdyrate at 80℃; for 1.5h; Neat (no solvent);93%
curcumin
458-37-7

curcumin

meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

thiourea
17356-08-0

thiourea

C29H26N2O6S

C29H26N2O6S

Conditions
ConditionsYield
With D-(+)-glucosamine hydrochloride In neat (no solvent) Microwave irradiation;96%
curcumin
458-37-7

curcumin

allyl bromide
106-95-6

allyl bromide

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

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

Conditions
ConditionsYield
With [benzene-1,3,5-triyltris(methylene)]tris(triphenylphosphonium) tribromide; sodium hydroxide In dichloromethane; water at 30℃; for 12h;96%
curcumin
458-37-7

curcumin

urea
57-13-6

urea

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(3,4-dihydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-one

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(3,4-dihydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With phosphomolybdic acid In ethanol for 0.0416667h; Microwave irradiation; Green chemistry;96%
4,5-Dichloro-1,2-phenylenediamine
5348-42-5

4,5-Dichloro-1,2-phenylenediamine

curcumin
458-37-7

curcumin

4,4'-((1E,1'E)-(7,8-dichloro-3H-benzo[b]-[1,4]-diazepine-2,4-diyl)bis(ethene-2,1-diyl))bis-(2-methoxyphenol)

4,4'-((1E,1'E)-(7,8-dichloro-3H-benzo[b]-[1,4]-diazepine-2,4-diyl)bis(ethene-2,1-diyl))bis-(2-methoxyphenol)

Conditions
ConditionsYield
With sulfuric acid In ethanol at 20℃;95.3%
curcumin
458-37-7

curcumin

(2-bromo-2-nitroethenyl)benzene
7166-19-0, 18315-81-6, 39674-40-3

(2-bromo-2-nitroethenyl)benzene

(2E)-1-(2-(3-hydroxy-4-methoxystyryl)-4,5-dihydro-5-nitro-4-phenylfuran-3-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one

(2E)-1-(2-(3-hydroxy-4-methoxystyryl)-4,5-dihydro-5-nitro-4-phenylfuran-3-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one

Conditions
ConditionsYield
With water; potassium carbonate In tetrahydrofuran at 20℃; for 2h; Feist-Benary reaction; Combinatorial reaction / High throughput screening (HTS); diastereoselective reaction;95%
ethyl 3-(chloroformyl)propionate
14794-31-1

ethyl 3-(chloroformyl)propionate

curcumin
458-37-7

curcumin

4,4'-((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-1,4-phenylene) diethyl disuccinate

4,4'-((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-1,4-phenylene) diethyl disuccinate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 2h; Inert atmosphere;95%
curcumin
458-37-7

curcumin

benzaldehyde
100-52-7

benzaldehyde

thiourea
17356-08-0

thiourea

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione
1373886-16-8

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione

Conditions
ConditionsYield
With tin(II) chloride dihdyrate at 80℃; for 1.33333h; Neat (no solvent);95%
With phosphomolybdic acid In ethanol for 0.0416667h; Microwave irradiation; Green chemistry;95%
With chitosan (viscosity 800–2000 cps) In water; acetic acid at 60℃; for 1.33333h; Green chemistry;94%
With piperidine In methanol at 60 - 65℃; for 16h;76%
curcumin
458-37-7

curcumin

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

thiourea
17356-08-0

thiourea

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-hydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-thione
1373886-21-5

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-hydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-thione

Conditions
ConditionsYield
With phosphomolybdic acid In ethanol for 0.0416667h; Microwave irradiation; Green chemistry;95%
With tin(II) chloride dihdyrate at 80℃; for 1.5h; Neat (no solvent);93%
curcumin
458-37-7

curcumin

salicylaldehyde
90-02-8

salicylaldehyde

thiourea
17356-08-0

thiourea

C29H26N2O6S

C29H26N2O6S

Conditions
ConditionsYield
With D-(+)-glucosamine hydrochloride In neat (no solvent) Microwave irradiation;95%
curcumin
458-37-7

curcumin

urea
57-13-6

urea

2,4-Dihydroxybenzaldehyde
95-01-2

2,4-Dihydroxybenzaldehyde

C29H26N2O8

C29H26N2O8

Conditions
ConditionsYield
With D-(+)-glucosamine hydrochloride In neat (no solvent) Microwave irradiation;95%
curcumin
458-37-7

curcumin

4-cyanobenzyl bromide
17201-43-3

4-cyanobenzyl bromide

C53H40N4O6

C53H40N4O6

Conditions
ConditionsYield
With [benzene-1,3,5-triyltris(methylene)]tris(triphenylphosphonium) tribromide; sodium hydroxide In dichloromethane; water at 30℃; for 12h;95%
curcumin
458-37-7

curcumin

4-bromobenzylidenemalononitrile
2826-24-6

4-bromobenzylidenemalononitrile

C30H25BrN2O6

C30H25BrN2O6

Conditions
ConditionsYield
With piperidine; dmap In ethanol for 12h; Reflux;95%
curcumin
458-37-7

curcumin

boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

2,2-difluoro-4,6-bis[β-(4-hydroxy-3-methoxystyryl)]-1,3,2-dioxaborine

2,2-difluoro-4,6-bis[β-(4-hydroxy-3-methoxystyryl)]-1,3,2-dioxaborine

Conditions
ConditionsYield
In dichloromethane at 20℃;95%
In tetrahydrofuran Reflux; Inert atmosphere;79%
In dichloromethane for 2h; Inert atmosphere; Reflux;510 mg
With acetic acid at 20℃; for 0.5h; Darkness;
In acetic acid at 20℃; for 0.5h; Sonication; Darkness;
curcumin
458-37-7

curcumin

acetic acid
64-19-7

acetic acid

((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene)diacetate
19697-86-0

((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene)diacetate

Conditions
ConditionsYield
With pyridine In dichloromethane at 155℃; for 1h;95%
curcumin
458-37-7

curcumin

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

urea
57-13-6

urea

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-methylphenyl)-3,4-dihydropyrimidin-2(1H)-one
1373886-15-7

5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-methylphenyl)-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With chitosan (viscosity 800–2000 cps) In water; acetic acid at 60℃; for 1.5h; Green chemistry;94%
With tin(II) chloride dihdyrate at 80℃; for 1.5h; Neat (no solvent);92%
With piperidine In methanol at 60 - 65℃; for 16h;81%

458-37-7Relevant articles and documents

Effects of Stable Degradation Products of Curcumin on Cancer Cell Proliferation and Inflammation

Sanidad, Katherine Z.,Zhu, Julia,Wang, Weicang,Du, Zheyuan,Zhang, Guodong

, p. 9189 - 9195 (2016)

Curcumin is among the most promising dietary compounds for cancer prevention. However, curcumin rapidly degrades in aqueous buffer at physiological pH, making it difficult to understand whether the effects of curcumin are from curcumin itself or its degradation products. Here we studied the antiproliferative and anti-inflammatory effects of curcumin degradation products, including its total degradation products (a mixture containing all stable degradation products of curcumin) and bicyclopentadione (a dominant stable degradation compound of curcumin). Curcumin potently modulated cell proliferation, progression of cell cycle, and apoptosis in MC38 colon cancer cells and inhibited lipopolysaccharide (LPS)-induced inflammatory responses and NF-κB signaling in RAW 264.7 macrophage cells. In contrast, neither the total degradation products of curcumin nor bicyclopentadione had such effects. For example, after 24 h of treatment in MC38 colon cancer cells, 5 μg/mL curcumin inhibited 39.2 ± 1.8% of cell proliferation, whereas its degradation products were inactive. Together, these results suggest that the stable chemical degradation products of curcumin are not likely to play a major role in mediating the biological activities of curcumin.

Stable isotope labeling strategy for curcumin metabolite study in human liver microsomes by liquid chromatography-tandem mass spectrometry

Gao, Dan,Chen, Xiaowu,Yang, Xiaomei,Wu, Qin,Jin, Feng,Wen, Hongliang,Jiang, Yuyang,Liu, Hongxia

, p. 686 - 694 (2015)

The identification of drug metabolites is very important in drug development. Nowadays, the most widely used methods are isotopes and mass spectrometry. However, the commercial isotopic labeled reagents are usually very expensive, and the rapid and convenient identification of metabolites is still difficult. In this paper, an 18O isotope labeling strategy was developed and the isotopes were used as a tool to identify drug metabolites using mass spectrometry. Curcumin was selected as a model drug to evaluate the established method, and the 18O labeled curcumin was successfully synthesized. The non-labeled and 18O labeled curcumin were simultaneously metabolized in human liver microsomes (HLMs) and analyzed by liquid chromatography/mass spectrometry (LC-MS). The two groups of chromatograms obtained from metabolic reaction mixture with and without cofactors were compared and analyzed using Metabolynx software (Waters Corp.; Milford, MA, USA). The mass spectra of the newly appearing chromatographic peaks in the experimental sample were further analyzed to find the metabolite candidates. Their chemical structures were confirmed by tandem mass spectrometry. Three metabolites, including two reduction products and a glucuronide conjugate, were successfully detected under their specific HLMs metabolic conditions, which were in accordance with the literature reported results. The results demonstrated that the developed isotope labeling method, together with post-acquisition data processing using Metabolynx software, could be used for fast identification of new drug metabolites.

Phenol radical cations and phenoxyl radicals in electron transfer from the natural phenols sesamol, curcumin and trolox to the parent radical cations of 1-chlorobutane

Joshi,Naumov,Kapoor,Mukherjee,Hermann,Brede

, p. 665 - 674 (2004)

The free electron transfer from sesamol, curcumin and trolox to solvent (1-chlorobutane) radical cations was studied. The solutes (ArOH) react with BuCl.+ at diffusion-controlled rates (~1010dm 3mol-1s-1/s

Asymmetric 1,5-diarylpenta-1,4-dien-3-ones: Antiproliferative activity in prostate epithelial cell models and pharmacokinetic studies

Zhang, Xiaojie,Guo, Shanchun,Chen, Chengsheng,Perez, German Ruiz,Zhang, Changde,Patanapongpibul, Manee,Subrahmanyam, Nithya,Wang, Rubing,Keith, Joshua,Chen, Guanglin,Dong, Yan,Zhang, Qiang,Zhong, Qiu,Zheng, Shilong,Wang, Guangdi,Chen, Qiao-Hong

, p. 263 - 279 (2017)

To further engineer dienones with optimal combinations of potency and bioavailability, thirty-four asymmetric 1,5-diarylpenta-1,4-dien-3-ones (25–58) have been designed and synthesized for the evaluation of their in vitro anti-proliferative activity in three human prostate cancer cell lines and one non-neoplastic prostate epithelial cell line. All these asymmetric dienones are sufficiently more potent than curcumin and their corresponding symmetric counterparts. The optimal dienone 58, with IC50 values in the range of 0.03–0.12 μM, is 636-, 219-, and 454-fold more potent than curcumin in three prostate cancer cell models. Dienones 28 and 49 emerged as the most promising asymmetric dienones that warrant further preclinical studies. The two lead compounds demonstrated substantially improved potency in cell models and superior bioavailability in rats, while exhibiting no acute toxicity in the animals at the dose of 10 mg/kg. Dienones 28 and 46 can induce PC-3 cell cycle regulation at the G0/G1 phase. However, dienone 28 induces PC-3 cell death in a different way from 46 even though they share the same scaffold, indicating that terminal heteroaromatic rings are critical to the action of mechanism for each specific dienone.

How curcumin works preferentially with water soluble antioxidants

Jovanovic,Boone,Steenken,Trinoga,Kaskey

, p. 3064 - 3068 (2001)

In this study we investigated physicochemical characteristics of the curcumin radical by pulse radiolysis and laser flash photolysis. Two methylated curcumin derivatives, methylcurcumin and trimethyl-curcumin, were synthesized to explore the role of phenol hydroxy and β-diketone moieties in the free radical chemistry of curcumin. Our results show that the initially generated β-oxo-alkyl transforms rapidly, probably via an intramolecular H-atom shift, into the phenoxyl-type curcumin radical. This phenoxyl does not react with oxygen, k 5 M-1 s-1, and can be repaired by any water-soluble antioxidant with appropriate redox potential, E6 6 M-1 s-1. A molecular mechanism of cancer chemoprevention by curcumin is proposed, with special emphasis on the synergism with water-soluble antioxidants.

Design and synthesis of new curcuminoid compounds and their derivatives as antioxidant agents

Abood, Rehab G.,Alsalim, Tahseen A.,Abood, Einas A.

, p. 2173 - 2183 (2021/04/22)

A series of new curcumin analogues and their derivatives were synthesized by reacting curcumin analogues with various substituted hydrazine compounds to afford new pyrazol derivatives. The preparation of ether and ester derivatives was also carried out. All synthesized compounds were characterized using FT-IR, 1HNMR, 13CNMR, and MS-ESI. The evaluations of these compounds have shown a good inhibition activity as antioxidant agents against the stable radical of diphenylpicrylhydrazyl (DPPH). Findings from this work demonstrated a high inhibition activity in compounds substituted with hydroxyl phenol groups in comparison with compounds with other groups.

Extraction of curcumin from turmeric powder through complexation

Rajasekharan, Kallikat Narayanan,Thomas, Sherin Geevarghese

, p. 695 - 699 (2021/07/10)

The complexation behavior of curcumin with boron and oxalic acid to form rubrocurcumin is utilized for the extraction of curcumin from turmeric powder. The complex formation reaction has been hastened by the addition of a phase transfer catalyst. To recover curcumin from the complex, the decomposition of the rubrocurcumin is studied. It was found that ammonia solution is a better reagent for the recovery of curcumin from its boron complex. The complexation of curcumin and its recovery by decomposition do not adversely affect curcumin, as ascertained by spectroscopic methods. This new approach for extraction of curcumin affords its isolation in an appreciable yield and in lesser time.

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