Xanthohumol - 10mM in DMSO , CAS No.6754-58-1

CAS: 6754-58-1 Cat. No.: X425397 Peso molecular: 354.4 Número EC: 614-078-4 PubChem CID: 639665

GRADE & PURITY 10mM in DMSO

Synonyms

Xanthohumol|6754-58-1|569-83-5|1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one|Xantho-flav|(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one|T4467YT1NT|CHEBI:6633

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Descripción general

Xanthohumol, also known as 2', 4, 4'-trihydroxy-6'-methoxy-3'-prenylchalcone or desmethylxanthohumol, is a member of the class of compounds known as 3-prenylated chalcones. It inhibits COX-1 and COX-2 activity and shows chemopreventive effects.

Specifications

Sinónimos

Xanthohumol | 6754-58-1 | 569-83-5 | 1-(2, 4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one | Xantho-flav | (E)-1-[2, 4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one | T4467YT1NT | CHEBI:6633

Especificaciones y pureza

10mM in DMSO

Mecanismos bioquímicos y fisiológicos

p97 ATPase (VCP) inhibitor. Binds to the N domain of p97, impairing autophagosome function and maturation. Inhibits proliferation and induces apoptosis in a variety of human cancer cell lines. Also inhibits DGAT in rat liver microsomes (IC50= 50.3μM).

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -80°C

Enviado en

Dry ice packs + Cold packs

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Nombres e identificadores

• Sonrisas canónicas: CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)C=CC2=CC=C(C=C2)O)O)C
• IUPAC Name: (E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• InChIKey: ORXQGKIUCDPEAJ-YRNVUSSQSA-N
• INCHI: 1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+
• Isómeros SMILES: CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)/C=C/C2=CC=C(C=C2)O)O)C
• WGK Alemania: 3
• PubChem CID: 639665
• Peso molecular: 354.4

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Clase Linear 1,3-diarylpropanoids
      • Subclass Chalcones and dihydrochalcones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: Linear 1,3-diarylpropanoids
• Subclass: Chalcones and dihydrochalcones
• Intermediate Tree Nodes: Not available
• Direct Parent: 3-prenylated chalcones
• Alternative Parents: 2'-Hydroxychalcones Cinnamylphenols Hydroxycinnamic acids and derivatives Methoxyphenols Styrenes Resorcinols Phenoxy compounds Anisoles Methoxybenzenes Aryl ketones Benzoyl derivatives 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Vinylogous acids Acryloyl compounds Enones Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: 3-prenylated chalcone - 2'-hydroxychalcone - Cinnamylphenol - Hydroxycinnamic acid or derivatives - Methoxyphenol - Phenoxy compound - Phenol ether - Resorcinol - Styrene - Aryl ketone - Anisole - Methoxybenzene - Benzoyl - Phenol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Benzenoid - Monocyclic benzene moiety - Acryloyl-group - Vinylogous acid - Enone - Alpha,beta-unsaturated ketone - Ketone - Ether - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.
• External Descriptors: Chalcones and dihydrochalcones

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)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

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CASP3 Tchem Caspase-3 (3632 Activities)

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PDPK1 Tchem 3-phosphoinositide dependent protein kinase-1 (3758 Activities)

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MAPK9 Tchem c-Jun N-terminal kinase 2 (4655 Activities)

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PRKCA Tchem Protein kinase C alpha (5923 Activities)

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PRKCQ Tchem Protein kinase C theta (3319 Activities)

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Homo sapiens (32628 Activities)

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BGC-823 (3035 Activities)

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Caco-2 (12174 Activities)

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CCRF-CEM (65223 Activities)

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DU-145 (51482 Activities)

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HT-29 (80576 Activities)

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MCF7 (126967 Activities)

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NCI-H1975 (4994 Activities)

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PC-3 (62116 Activities)

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SGC-7901 (2773 Activities)

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T98G (1524 Activities)

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U-87 MG (3946 Activities)

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A549 (127892 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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HUVEC (11049 Activities)

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Ishikawa (877 Activities)

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LNCaP (8286 Activities)

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HeLa (62764 Activities)

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SETD7 Tchem Histone-lysine N-methyltransferase SETD7 (390 Activities)

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DGAT1 Tclin Diacylglycerol O-acyltransferase 1 (1719 Activities)

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Liver (3974 Activities)

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MAPK3 Tchem Mitogen-activated protein kinase; ERK1/ERK2 (651 Activities)

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MAPK13 Tchem MAP kinase p38 (1586 Activities)

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NFKB2 Tchem Nuclear factor NF-kappa-B complex (2307 Activities)

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LY96 Tchem Lymphocyte antigen 96 (117 Activities)

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LNCaP C4-2 (165 Activities)

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Objetivos asociados (no humanos)

Ttr Transthyretin (14 Activities)

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PTGES Prostaglandin E synthase (10 Activities)

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Plasmodium falciparum (966862 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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MEF (1005 Activities)

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RAW264.7 (28094 Activities)

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BV-2 (3710 Activities)

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TRXR Thioredoxin reductase (20 Activities)

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Nqo1 NAD(P)H dehydrogenase [quinone] 1 (1058 Activities)

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Akt1 RAC-alpha serine/threonine-protein kinase (147 Activities)

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Bcl2l1 Bcl-2-like protein 1 (1 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Sensibilidad: Light Sensitive,Air Sensitive,Heat Sensitive
• Punto de fusión (°C): 159 °C
• Peso molecular: 354.400 g/mol
• XLogP3: 5.100
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 354.147 Da
• Monoisotopic Mass: 354.147 Da
• Topological Polar Surface Area: 87.000 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 514.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Referencias

1. Fa-Li Zhang, Liu Yang, Wei-Hao He, Ling-Jun Xie, Fei Yang, Ying-Hui Wang, Ai-Guo Huang.  (2023)  In vivo antibacterial activity of medicinal plant Sophora flavescens against Streptococcus agalactiae infection.  JOURNAL OF FISH DISEASES,  46  (9): (977-986).  [PMID:37294673] [10.1111/jfd.13818]

2. Wei Liu, Xiao Chen, Chen Yang, Zequn Lin, Xinfeng Huang, Zhen Zhang, Jianjun Liu.  (2025)  Preventive effects of xanthohumol in APP/PS1 mice based on multi-omics atlas.  BRAIN RESEARCH BULLETIN,      [PMID:40132750] [10.1016/j.brainresbull.2025.111316]

3. Liu Wei, Chen Xiao, Zhao Jing, Yang Chen, Huang Guanqin, Zhang Zhen, Liu Jianjun.  (2024)  Protective signature of xanthohumol on cognitive function of APP/PS1 mice: a urine metabolomics approach by age.  Frontiers in Pharmacology,      [PMID:39114364] [10.3389/fphar.2024.1423060]

4. Yan Gao, Zilin Song, Wenxin Gan, Xue Zou, Yaning Bai, Xiuli Zhao, Dawei Chen, Mingxi Qiao.  (2025)  Selective and iron-independent ferroptosis in cancer cells induced by manipulation of mitochondrial fatty acid oxidation.  BIOMATERIALS,      [PMID:40112511] [10.1016/j.biomaterials.2025.123259]

5. Han Ning, Li Jie, Li Yangyang, Zhao Feiei, Wang Jun, Ye Peiyu, Zeng Zhenling.  (2024)  Xanthohumol ameliorates dextran sodium sulfate-induced colitis in mice by inhibiting of NF-κB signaling pathways and modulating intestinal microbiota.  EUROPEAN JOURNAL OF NUTRITION,  64  (1): (1-13).  [PMID:39576384] [10.1007/s00394-024-03525-5]

6. Aiguo Huang, Yanqin Wei, Jialong Huang, Songlin Luo, Tingyu Wei, Jing Guo, Fali Zhang, Yinghui Wang.  (2025)  Effects of Natural Ingredient Xanthohumol on the Intestinal Microbiota, Metabolic Profiles and Disease Resistance to Streptococcus agalactiae in Tilapia Oreochromis niloticus.  Microorganisms,  13  (7): (1699).  [PMID:40732208] [10.3390/microorganisms13071699]

7. Wen Yan, Ying Huang, Yanjie Zhou, Qingfang Xie, Wanbin Huang, Yuexiu Lei, Zheman Xiao.  (2026)  Xanthohumol alleviates central sensitization in migraine via PPARα-mediated activation of the AMPK pathway and suppression of neuroinflammation.  PHYTOMEDICINE,      [PMID:41539101] [10.1016/j.phymed.2026.157816]