BIS(4-HYDROXYCINNAMOYL)METHANE

Product Name: BIS(4-HYDROXYCINNAMOYL)METHANE
CAS No.: 33171-05-0
Chemical Name: BIS(4-HYDROXYCINNAMOYL)METHANE
Synonyms: BISDEMETHOXY CURCUMIN;CURCUMIN 3;Misdemeanour;Didemethoxycurcumin;BIS-DESMETHOXYCURCUMIN;DEMETHOXYCURCUMIN, BIS-;Bisdemethoxycurcumin(b);(E,E)-BisdeMethoxycurcuMin;Bisdemethoxycurcumin(BDMC);BIS(4-HYDROXYCINNAMOYL)METHANE
CBNumber: CB9180475
Molecular Formula: C19H16O4
Formula Weight: 308.33
MOL File: 33171-05-0.mol

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BIS(4-HYDROXYCINNAMOYL)METHANE Property

Melting point:: 221-223 ºC
Boiling point:: 551.3±45.0 °C(Predicted)
Density: 1.285
storage temp.: 2-8°C
solubility: DMSO (Slightly), Methanol (Slightly, Heated)
pka: 8.50±0.46(Predicted)
form: solid
color: Orange to Dark Orange
BRN: 3149384
Stability:: Light Sensitive
InChI: InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+
InChIKey: PREBVFJICNPEKM-YDWXAUTNSA-N
SMILES: C(/C1=CC=C(O)C=C1)=C\C(=O)CC(=O)/C=C/C1=CC=C(O)C=C1
LogP: 3.155 (est)

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Safety

WGK Germany: 3
HS Code: 29145090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: B6938
Product name: Bisdemethoxycurcumin
Purity: ≥98% (HPLC), solid
Packaging: 5mg
Price: $121
Updated: 2025/07/31

Sigma-Aldrich

Product number: PHR3434
Product name: Bisdesmethoxycurcumin
Purity: certified reference material, pharmaceutical secondary standard
Packaging: 50MG
Price: $227.05
Updated: 2025/07/31

Sigma-Aldrich

Product number: 90594
Product name: Bisdemethoxycurcumin
Purity: analytical standard
Packaging: 10mg
Price: $332
Updated: 2025/07/31

Sigma-Aldrich

Product number: 1075305
Product name: Bisdesmethoxycurcumin
Purity: UnitedStatesPharmacopeia(USP)ReferenceStandard
Packaging: 30mg
Price: $375
Updated: 2025/07/31

TCI Chemical

Product number: B6548
Product name: Bisdemethoxycurcumin
Packaging: 1G
Price: $129
Updated: 2025/07/31

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BIS(4-HYDROXYCINNAMOYL)METHANE Chemical Properties,Usage,Production

Uses

Bisdemethoxycurcumin is one of the three major forms of curcuminoids found in the rhizomes of turmeric. Bisdemethoxycurcumin displays antioxidant, anti-inflammatory as well as chemotherapeutic activit y. Bisdemethoxycurcumin acts as an inhibitor of human pancreatic α-amylase, a target for type-2 diabetes .

Uses

Bisdemethoxycurcumin has been used:

to test its inhibitory effect on cell cycle and mitochondrial function in gastric adenocarcinoma cells
to test it neuroprotective role against lead (Pb) induced toxicity in dopaminergic and noradrenergic systems of Meriones shawi
as a standard for calibration curve generation to quantify plasma curcuminoids using high-performance liquid chromatography-diode array detection (HPLC-DAD) and ultraviolet (UV)

Definition

ChEBI: Bisdemethoxycurcumin is a beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups. It has a role as a metabolite and an EC 3.2.1.1 (alpha-amylase) inhibitor. It is a beta-diketone, a polyphenol, an enone and a diarylheptanoid. It is functionally related to a 4-coumaric acid.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Bisdemethoxycurcumin (BDMC) is a derivative or curcumin, and represents one of the major active components of curcumin products isolated from Curcumae sp. BDMC shares similar anti-inflammatory properties with demethoxycurcumin. It inhibits LPS-induced nitric oxide (NO) production and expression of iNOS and COX2 in RAW264.7 cells by blocking NF-kB activation. BDMC also displays unique properties in that it enhances Abeta clearance by upregulating expression MGAT3 and TLR genes. BDMC potently inhibits AKR1B10.

Synthesis

123-08-0

123-54-6

22608-12-4

GENERAL METHOD: Acetylacetone (10 mmol) was dissolved in ethyl acetate (30 mL), boronic anhydride (5.0 mmol) was added, followed by 4-hydroxybenzaldehyde (20 mmol) and tributyl borate (40 mmol). The reaction mixture was stirred at 50 °C for 10 min. Then, a solution of n-butylamine (5.0 mmol) in ethyl acetate (5 mL) was slowly added dropwise at 50 °C. After the dropwise addition, the reaction temperature was raised to 80 °C and stirring was continued for 4 hours. After completion of the reaction, the reaction was quenched by the addition of 1N hydrochloric acid (30 mL) and stirring was continued for 40 minutes. The organic layer was separated, washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was recrystallized from methanol to give the target product bisdemethoxycurcumin (1a or 1b) as a yellow solid.

References

[1] Molecules, 2011, vol. 16, # 2, p. 1888 - 1900
[2] Molecules, 2014, vol. 19, # 10, p. 16349 - 16372
[3] Archiv der Pharmazie, 2004, vol. 337, # 1, p. 42 - 54
[4] Food Chemistry, 2010, vol. 119, # 4, p. 1435 - 1442
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 23, p. 6374 - 6380

BIS(4-HYDROXYCINNAMOYL)METHANE Preparation Products And Raw materials

Raw materials

Preparation Products

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BIS(4-HYDROXYCINNAMOYL)METHANE Suppliers

Canada 1 China 229 Germany 1 India 3 Japan 2 United Kingdom 1 United States 18 Global 255

Hangzhou Great Forest Biomedical Ltd.

Tel: 0571-28313180 17767135330
Fax: 0571-28313182
Email: info@great-forest.com
Country: China
ProdList: 54
Advantage: 58

Chengdu Wuyuan Bioengineering Co., Ltd.

Tel: 17358513851
Email: henry851@163.com
Country: China
ProdList: 955
Advantage: 58

Suzhou Uugene Biopharma Co., Ltd.

Tel: 0512-69561956 18015581618
Email: sales@uugene.com
Country: China
ProdList: 101
Advantage: 55

J & K SCIENTIFIC LTD.

Tel: 18210857532; 18210857532
Fax: 86-10-82849933
Email: jkinfo@jkchemical.com
Country: China
ProdList: 96815
Advantage: 76

Chembest Research Laboratories Limited

Tel: +86-21-20908456
Fax: 021-58180499
Email: sales@BioChemBest.com
Country: China
ProdList: 6003
Advantage: 61

Beijing HwrkChemical Technology Co., Ltd

Tel: 18515581800 18501085097
Fax: 010-89508210
Email: sales.bj@hwrkchemical.com
Country: China
ProdList: 9400
Advantage: 55

JinYan Chemicals(ShangHai) Co.,Ltd.

Tel: 13817811078
Fax: 86-021-50426522,50426273
Email: sales@jingyan-chemical.com
Country: China
ProdList: 9976
Advantage: 60

Nanjing Chemlin Chemical Co., Ltd

Tel: 025-83697070
Fax: +86-25-83453306
Email: info@chemlin.com.cn
Country: China
ProdList: 15883
Advantage: 64

China DongFan Chemical Co.,LTD

Tel: 86-0571-85151182
Fax: 86-0571-85151182
Country: China
ProdList: 5691
Advantage: 66

Shandong Xiya Chemical Co., Ltd

Tel: 4009903999 13355009207
Fax: 0539-6365991
Email: 3007715519@qq.com
Country: China
ProdList: 18729
Advantage: 57

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View Lastest Price from BIS(4-HYDROXYCINNAMOYL)METHANE manufacturers

Hebei Zhuanglai Chemical Trading Co Ltd

Product: BIS(4-HYDROXYCINNAMOYL)METHANE 33171-05-0
Price: US $55.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20 tons
Release date: 2024-11-26

BINBO BIOLOGICAL CO.,LTD

Product: Bisdemethoxycurcumin (BDMC) 33171-05-0
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99.8%
Supply Ability: 1000 kg
Release date: 2024-04-02

PNP Biotech Co. Ltd

Product: Bisdemethoxycurcumin 33171-05-0
Price: US $0.00/kg
Min. Order: 25kg
Purity: 6.04%
Supply Ability: Inquiry
Release date: 2022-10-25

33171-05-0, BIS(4-HYDROXYCINNAMOYL)METHANERelated Search:

4-Methoxybenzoic acid Octyl 4-methoxycinnamate 5"-MethoxyhexahydrocurcuMin DihydrocurcuMin FLLL31 ASC-J9 (3S,5S)-1,7-BIS(4-HYDROXY-3-METHOXYPHENYL)HEPTANE-3,5-DIOL HEXAHYDROCURCUMIN Tetrahydrocurcumin DEMETHOXYCURCUMIN 1,4-HEXADIENE BIS(4-HYDROXYCINNAMOYL)METHANE,BIS-(PARA-HYDROXYCINNAMOYL)METHANE DEMETHOXYCURCUMIN Curcumin

(1E,6E)-1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione

PARAPARADIHYDROXYDICINNAMOYLMETHANE

(E,E)-BisdeMethoxycurcuMin

(E,E)-1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione

CURCUMIN 3

DEMETHOXYCURCUMIN, BIS-

BISDEMETHOXY CURCUMIN

BIS-DESMETHOXYCURCUMIN

BIS(4-HYDROXYCINNAMOYL)METHANE

Bisdemethoxycurcumin, 98%, from Zingiber officinale Rosc.

Didemethoxycurcumin

1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-, (E,E)-

Bis(p-hydroxycinnamoyl)methane

Deleted CAS No: 22608-12-4, 85801-92-9, 91884-88-7, 104024-29-5

Bisdemethoxycurcumin(BDMC)

Bisdemethoxycurcumin(b)

1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-, (1E,6E)-

BIS(4-HYDROXYCINNAMOYL)METHANE USP/EP/BP

Misdemeanour

(1E,6E)-Bis(demethoxy)curcumin

(E,E)-Curcumin III,Bisdemethoxycurcumin,inhibit,(E,E)-Didemethoxycurcumin,Inhibitor,Apoptosis,Autophagy,(E,E)-Bisdemethoxycurcumin

Bisdemethoxycurcumin/1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-, (1E,6E)-

Bisdemethoxycurcumin, Apoptotic curcuminoid

(E,E)-Bisdemethoxycurcumin - Bio-X ?

33171-05-0

34939-16-0

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