Bisdemethoxycurcumin - ≥98%(HPLC) , CAS No.33171-05-0

CAS: 33171-05-0 Cat. No.: B133654 Peso molecular: 308.33 Beilstein Registry Number: 3149384 Número EC: 881-423-5

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

Room temperature

Shipped In

Normal

Descripción general

Bisdemethoxycurcumin(Curcumin III; Didemethoxycurcumin) is a natural derivative of curcumin with anti-inflammatory and anti-cancer activities.

Specifications

Sinónimos

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

Especificaciones y pureza

≥98%(HPLC)

Mecanismos bioquímicos y fisiológicos

Apoptotic anticancer, anti-inflammatory and antioxidant curcuminoid. Inhibits wnt activity through activation of WIF-1. Induces demethylation through DNA methyltransferase 1 inhibition. Potent and competitive aldo-keto reductase inhibitor (K i = 22 nM).

Condiciones de almacenamiento de almacenamiento

Room temperature

Enviado en

Normal

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%(HPLC)

Nombres e identificadores

• Sonrisas canónicas: 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+
• Isómeros SMILES: C1=CC(=CC=C1/C=C/C(=O)CC(=O)/C=C/C2=CC=C(C=C2)O)O
• Peso molecular: 308.33
• Beilstein: 3149384
• 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
    • Clase Diarylheptanoids
      • Subclass Linear diarylheptanoids

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: 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
• Descripción: 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

Objetivos asociados (humanos)

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

Discover Target: AKR1B10

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

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

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

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

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

MAOB Tclin Monoamine oxidase B (8835 Activities)

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

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

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

Discover Target: DNMT1

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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CAMK2A Tchem CaM kinase II alpha (1938 Activities)

Discover Target: CAMK2A

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)

Discover Target: MAPK13

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

SMAD2 Tbio Mothers against decapentaplegic homolog 2 (9 Activities)

Discover Target: SMAD2

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

Objetivos asociados (no humanos)

Glo1 Glyoxalase I (4 Activities)

Discover Target: Glo1

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

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)

Discover Target: sssIM

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srtA Sortase A (641 Activities)

Discover Target: srtA

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TOP2 DNA topoisomerase 2 (10 Activities)

Discover Target: TOP2

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Luciferin 4-monooxygenase (66902 Activities)

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TOP1 DNA topoisomerase 1 (4 Activities)

Discover Target: TOP1

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BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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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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Mecanismos de acción

Propiedades químicas y físicas

• Peso molecular: 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

Referencias

1. 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]

2. 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]

3. Haoyu Yang, Xin Chen, Siqi Huang, Hongfang Dai, Zuowei Xiao, Jialong Fan, Honggang Zhang, Ke Du, Yan Qin.  (2025)  A novel GSH depletor for simultaneous ferroptosis and cuproptosis Activation in hepatocellular carcinoma.  BIOCHEMICAL PHARMACOLOGY,      [PMID:41173053] [10.1016/j.bcp.2025.117488]