MilliporeSigma
All Photos(1)

Documents

B6938

Sigma-Aldrich

Bisdemethoxycurcumin

≥98% (HPLC), solid

Sign Into View Organizational & Contract Pricing

Synonym(s):
(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
Empirical Formula (Hill Notation):
C19H16O4
Molecular Weight:
308.33
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

solid

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

SMILES string

Oc1ccc(cc1)\C=C\C(=O)CC(=O)\C=C\c2ccc(O)cc2

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+

InChI key

PREBVFJICNPEKM-YDWXAUTNSA-N

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
F9057SML081990594
Bisdemethoxycurcumin ≥98% (HPLC), solid

B6938

Bisdemethoxycurcumin

FLLL31 ≥98% (HPLC)

F9057

FLLL31

Sigma-Aldrich

SML0819

Bisdionin C

Bisdemethoxycurcumin analytical standard

90594

Bisdemethoxycurcumin

form

solid

form

powder

form

powder

form

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

solubility

DMSO: ≥20 mg/mL

solubility

DMSO: ≥10 mg/mL

solubility

DMSO: 1 mg/mL, clear (warmed)

solubility

-

Application

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)

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.
Bisdemethoxycurcumin (BMDC) is a stable dimethoxy derivative of curcumin and is useful as a supplement in cell culture medium. It also possesses antimicrobial, antioxidative and neuroprotective functionality.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 9

1 of 9

Curcumin primary reference standard

00280590

Curcumin

Curcumin from Curcuma longa (Turmeric), powder

Sigma-Aldrich

C1386

Curcumin

Hexahydrocurcumin analytical standard

Supelco

69727

Hexahydrocurcumin

Curcumin for synthesis

Sigma-Aldrich

8.20354

Curcumin

Desmethoxycurcumin United States Pharmacopeia (USP) Reference Standard

USP

1173100

Desmethoxycurcumin

Curcumin phyproof® Reference Substance

PHL89180

Curcumin

Tetrahydrocurcumin analytical standard

Supelco

50202

Tetrahydrocurcumin

USP

USP

1151866

Curcuminoids

Ciclopirox olamine European Pharmacopoeia (EP) Reference Standard

C2162700

Ciclopirox olamine

Brazilian Curcuma longa L. attenuates comorbidities by modulating adipose tissue dysfunction in obese rats
Lo ATC, et al.
Nutrire, 43(1), 25-25 (2018)
Lahcen Tamegart et al.
Comptes rendus biologies, 342(5-6), 192-198 (2019-09-03)
Exposure to lead is a threat factor for neurodegenerative disorders progress as it could trigger dopaminergic deficiency. We aimed herein to assess the effect of acute lead exposure (25mg/kg B.W i.p.) during three continuous days on the dopaminergic and noradrenergic
Changjiang Luo et al.
Oncology letters, 9(1), 270-274 (2014-12-02)
Bisdemethoxycurcumin (BDMC) is a demethoxy derivative of curcumin. In this study, a human gastric adenocarcinoma xenograft model was generated in vivo using nude mice and BDMC was observed to suppress the growth and activity of tumors, in addition to improving
Wojciech Ostrowski
European journal of mass spectrometry (Chichester, England), 21(1), 45-50 (2015-04-24)
Curcumin complexes with iron ions were investigated by electrospray ionization mass spectrometry. It was shown that in methanol solutions of curcumin and iron(III) ions, complexes are formed with a stoichiometry of 1 : 1, 2 : or 3 : 1.
Hannelore Rücker et al.
Organic & biomolecular chemistry, 13(10), 3040-3047 (2015-01-27)
Inflammatory signaling pathways orchestrate the cellular response to infection and injury. These pathways are known to be modulated by compounds that alkylate cysteinyl thiols. One class of phytochemicals with strong thiol alkylating activity is the chalcones. In this study we

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service