Bisdemethoxycurcumin - ≥98%(HPLC) , CAS No.24939-16-0

CAS: 24939-16-0 Cat. No.: B131602 Molecular Weight: 308.328 EC Number: 607-464-9

GRADE & PURITY ≥98%(HPLC)

Synonyms

Bisdemethoxycurcumin | CHEBI:71045 | UNII-2EFO1BP34R | Curcumin III;Didemethoxycurcumin | Dide Methoxycurcu Min | Direct Green MB | (1E,6E)-1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione | AC-24239 | AC-34720 | 1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydro

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia

Specifications

Synonyms

Bisdemethoxycurcumin | CHEBI:71045 | UNII-2EFO1BP34R | Curcumin III;Didemethoxycurcumin | Dide Methoxycurcu Min | Direct Green MB | (1E, 6E)-1, 7-Bis(4-hydroxyphenyl)-1, 6-heptadiene-3, 5-dione | AC-24239 | AC-34720 | 1, 6-Heptadiene-3, 5-dione, 1, 7-bis(4-hydro

Specifications & Purity

≥98%(HPLC)

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 488195329
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195329
• Canonical Smiles: C1=CC(=CC=C1C=CC(=O)CC(=O)C=CC2=CC=C(C=C2)O)O
• IUPAC Name: (1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
• InChIKey: PREBVFJICNPEKM-YDWXAUTNSA-N
• 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+
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C(=O)CC(=O)/C=C/C2=CC=C(C=C2)O)O
• Alternate CAS: 33171-05-0
• Molecular Weight: 308.328
• Reaxy-Rn: 2144744
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2144744&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Diarylheptanoids
      • Subclass Linear diarylheptanoids

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Diarylheptanoids
• Subclass: Linear diarylheptanoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Curcuminoids
• Alternative Parents: Hydroxycinnamic acids and derivatives Styrenes Beta-diketones 1-hydroxy-2-unsubstituted benzenoids Enones Acryloyl compounds Ketones Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Bis-desmethoxycurcumin - Hydroxycinnamic acid or derivatives - Styrene - 1-hydroxy-2-unsubstituted benzenoid - Phenol - 1,3-diketone - Benzenoid - 1,3-dicarbonyl compound - Monocyclic benzene moiety - Enone - Acryloyl-group - Alpha,beta-unsaturated ketone - Ketone - Organic oxide - Organooxygen compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.
• External Descriptors: enone - polyphenol - beta-diketone - diarylheptanoid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

AKR1B10 Tchem Aldo-keto reductase family 1 member B10 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ACHE Tclin Acetylcholinesterase (18204 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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MAOB Tclin Monoamine oxidase B (8835 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AKR1B1 Tclin Aldose reductase (1404 Activities)

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DNMT1 Tclin DNA (cytosine-5)-methyltransferase 1 (978 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APP Tclin Amyloid-beta A4 protein (8510 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CAMK2A Tchem CaM kinase II alpha (1938 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TERT Tchem Telomerase reverse transcriptase (2428 Activities)

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Caco-2 (12174 Activities)

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DLD-1 (17511 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-1080 (3966 Activities)

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HT-29 (80576 Activities)

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MCF7 (126967 Activities)

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MT4 (17854 Activities)

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OVCAR-3 (48710 Activities)

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PC-3 (62116 Activities)

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SK-OV-3 (52876 Activities)

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A549 (127892 Activities)

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EOL1 (427 Activities)

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A-431 (6446 Activities)

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HEK293 (82097 Activities)

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HepG2 (196354 Activities)

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NCI-H460 (60772 Activities)

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KB (17409 Activities)

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LNCaP (8286 Activities)

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MDA-MB-231 (73002 Activities)

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PBMC (10003 Activities)

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WRL68 (207 Activities)

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AKR1B10 Tchem Aldo-keto reductase family 1 member B10 (300 Activities)

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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

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MAPK13 Tchem MAP kinase p38 (1586 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SMAD2 Tbio Mothers against decapentaplegic homolog 2 (9 Activities)

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Associated Targets(non-human)

Glo1 Glyoxalase I (4 Activities)

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pol Human immunodeficiency virus type 1 integrase (9041 Activities)

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Staphylococcus aureus (210822 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Trypanosoma brucei brucei (13300 Activities)

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Leishmania major (2877 Activities)

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Leishmania mexicana (936 Activities)

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Mus musculus (284745 Activities)

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CHO (4503 Activities)

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PC-12 (7051 Activities)

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Vero (26788 Activities)

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HT-22 (3261 Activities)

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sssIM CpG DNA methylase (38 Activities)

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srtA Sortase A (641 Activities)

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TOP2 DNA topoisomerase 2 (10 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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TOP1 DNA topoisomerase 1 (4 Activities)

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BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CDR1 Multidrug resistance protein CDR1 (48 Activities)

Discover Target: CDR1

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 224°C
• Molecular Weight: 308.300 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 308.105 Da
• Monoisotopic Mass: 308.105 Da
• Topological Polar Surface Area: 74.600 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 408.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

References

1. Xiaoqin Ding, Yan Chen, Lina Zhou, Ruoyun Wu, Tunyu Jian, Han Lyu, Yan Liu, Jian Chen.  (2022)  Bisdemethoxycurcumin Attenuated Renal Injury via Activation of Keap1/Nrf2 Pathway in High-Fat Diet-Fed Mice.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  23  (13): (7395).  [PMID:35806399] [10.3390/ijms23137395]

2. Dai Chongshan, Ciccotosto Giuseppe D., Cappai Roberto, Tang Shusheng, Li Daowen, Xie Sanlei, Xiao Xilong, Velkov Tony.  (2016)  Curcumin Attenuates Colistin-Induced Neurotoxicity in N2a Cells via Anti-inflammatory Activity, Suppression of Oxidative Stress, and Apoptosis.  MOLECULAR NEUROBIOLOGY,  55  (1): (421-434).  [PMID:27957686] [10.1007/s12035-016-0276-6]

3. Xiuying Liu, Lijie Zhu, Xue Gao, Yuxin Wang, Haixia Lu, Yiwei Tang, Jianrong Li.  (2016)  Magnetic molecularly imprinted polymers for spectrophotometric quantification of curcumin in food.  FOOD CHEMISTRY,      [PMID:26920299] [10.1016/j.foodchem.2016.02.015]