α-Naphthoflavone - 10mM in DMSO , CAS No.604-59-1

CAS: 604-59-1 Cat. No.: N425015 Formula: C19H12O2 Peso molecolare: 272.3 Beilstein Registry Number: 210494 Numero EC: 210-071-1
Disponibile su ordine
GRADE & PURITY 10mM in DMSO
Synonyms
2-phenyl-4-benzo[h][1]benzopyranone | DTXSID2040650 | A-NAPHTHYLFLAVONE | CCRIS-3607 | F16466 | alpha -Naphthoflavone | alpha-Naphthoflavone | BDBM50014323 | HMS3740O15 | FML65D8PY5 | 2-Phenyl-4H-naphtho(1,2-b)pyran-4-one | .alpha.-Naphthylflavone | 4H-Na
Storage
Store at -80°C
Shipped In
Dry ice packs + Cold packs
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Size
Germania (EU)
USA*
Price
Qty
1ml
N425015-1ml
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51,11€

60,65€
Salva 9,55 € (15.74%)
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Why this grade

10mM in DMSO for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Store at -80°C Ships Dry ice packs + Cold packs Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 12 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Panoramica

α-Naphthoflavone is a naturally occurring compound found in Passiflora. α-Naphthoflavone is an aryl hydrocarbon receptor antagonist and inhibitor of CYP1A1 gene expression. Experiments show inhibitory properties towards cytochrome P450 enzymes, CYP1A1 (P4501A1) and CYP1A2 (P4501A2) (competetive binding) with stimulatory activities towards CYP3A4 (P4503A4) (selective binding). α-Naphthoflavone is an inhibitor of CYP19.
An aryl hydrocarbon receptor inhibitor.

Specifications

Sinonimi
2-phenyl-4-benzo[h][1]benzopyranone | DTXSID2040650 | A-NAPHTHYLFLAVONE | CCRIS-3607 | F16466 | alpha -Naphthoflavone | alpha-Naphthoflavone | BDBM50014323 | HMS3740O15 | FML65D8PY5 | 2-Phenyl-4H-naphtho(1,2-b)pyran-4-one | .alpha.-Naphthylflavone | 4H-Na
Specifiche e purezza
10mM in DMSO
Condizioni di conservazione di stoccaggio
Store at -80°C
Spedito in
Dry ice packs + Cold packs
Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.
Nomi e identificatori
Pubchem Sid528768813
Sorrisi canoniciC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C4=CC=CC=C4C=C3
IUPAC Name2-phenylbenzo[h]chromen-4-one
InChIKeyVFMMPHCGEFXGIP-UHFFFAOYSA-N
INCHI1S/C19H12O2/c20-17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H
Isomeri SMILES C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C4=CC=CC=C4C=C3
WGK Germania 3
RTECS QL6250000
Numero UN 1325
Peso molecolare 272.3
Beilstein 210494
Reaxy-Rn 210862
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=210862&ln=

Documentazione

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

Download SDS →

✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

Look up COA →

📊 Datasheet

Quick-reference summary of product specifications and applications.

View datasheet →

🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

View spec sheet →

Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClasseFlavonoids
SubclassFlavones
Intermediate Tree Nodes Not available
Direct ParentFlavones
Alternative Parents Naphthopyranones  Chromones  Naphthalenes  Pyranones and derivatives  Benzene and substituted derivatives  Heteroaromatic compounds  Oxacyclic compounds  Organooxygen compounds  Organic oxides  Hydrocarbon derivatives  
Molecular FrameworkAromatic heteropolycyclic compounds
Substituents Flavone - Naphthopyranone - Naphthopyran - Chromone - Benzopyran - Naphthalene - 1-benzopyran - Pyranone - Pyran - Monocyclic benzene moiety - Benzenoid - Heteroaromatic compound - Organoheterocyclic compound - Oxacycle - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aromatic heteropolycyclic compound
DescrizioneThis compound belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
External Descriptors a small molecule
Struttura 3D
Modello di struttura chimica interattiva





Obiettivi associati (umani)
CYP1A2 Tchem Cytochrome P450 1A2 (31 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
CYP1B1 Tchem Cytochrome P450 1B1 (25 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
CYP19A1 Tclin Aromatase (2 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
CYP1A1 Tchem Cytochrome P450 1A1 (20 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
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ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)
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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
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AR Tclin Androgen Receptor (11781 Activities)
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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
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CYP19A1 Tclin Cytochrome P450 19A1 (6099 Activities)
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DRD2 Tclin Dopamine D2 receptor (23596 Activities)
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DRD1 Tclin Dopamine D1 receptor (9720 Activities)
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DRD4 Tchem Dopamine D4 receptor (7907 Activities)
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ACHE Tclin Acetylcholinesterase (18204 Activities)
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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)
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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
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HRH2 Tclin Histamine H2 receptor (5428 Activities)
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ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)
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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)
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CALCR Tclin Calcitonin receptor (2215 Activities)
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SLC6A4 Tclin Serotonin transporter (12625 Activities)
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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
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HRH1 Tclin Histamine H1 receptor (7573 Activities)
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ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRM1 Tclin Mu opioid receptor (19785 Activities)
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DRD3 Tclin Dopamine D3 receptor (14368 Activities)
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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)
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OPRD1 Tclin Delta opioid receptor (15096 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRK1 Tclin Kappa opioid receptor (16155 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
XDH Tclin Xanthine dehydrogenase (1038 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A3 Tclin Dopamine transporter (10535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR4 Tclin Serotonin 4 (5-HT4) receptor (2068 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR2 Tclin Estrogen receptor beta (9272 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYSLTR1 Tclin Cysteinyl leukotriene receptor 1 (2118 Activities)
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Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)
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Mc4r Melanocortin receptor 4 (1205 Activities)
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Ltc4s Leukotriene C4 synthase (1 Activities)
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Sigmar1 Sigma opioid receptor (160 Activities)
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Npy1r Neuropeptide Y receptor type 1 (8 Activities)
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Cruzipain (33337 Activities)
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Cckar Cholecystokinin A receptor (90 Activities)
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Abcc1 Multidrug resistance-associated protein 1 (42 Activities)
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Abcb1b P-glycoprotein 1 (174 Activities)
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Nos2 Nitric oxide synthase, inducible (3573 Activities)
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Mapk1 MAP kinase ERK2 (650 Activities)
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Mmp9 Matrix metalloproteinase 9 (38 Activities)
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Rattus norvegicus (775804 Activities)
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lef Anthrax lethal factor (7585 Activities)
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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)
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CYP3A6 Cytochrome P450 3A6 (2 Activities)
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Glra2 Glycine receptor (1745 Activities)
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Meccanismi d'azione
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
SensibilitàLight sensitive
Punto di fusione (°C)155-158°C
Peso molecolare272.300 g/mol
XLogP34.800
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass272.084 Da
Monoisotopic Mass272.084 Da
Topological Polar Surface Area26.300 Ų
Heavy Atom Count21
Formal Charge0
Complexity433.000
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Citations of This Product
Riferimenti
1. Shuaishuai Chen, Weiyu Guo, Huan Liu, Jiang Zheng, Dingyan Lu, Jia Sun, Chun Li, Chunhua Liu, Yonglin Wang, Yong Huang, Wen Liu, Yongjun Li, Ting Liu.  (2023)  Mechanistic study of cytochrome P450 enzyme-mediated cytotoxicity of psoralen and isopsoralen.  FOOD AND CHEMICAL TOXICOLOGY,      [PMID:37660943] [10.1016/j.fct.2023.114011]
2. Xiaole Zhao, Xiaoyong Huang, Wenjing Peng, Muke Han, Xin Zhang, Kui Zhu, Bing Shao.  (2022)  Chlorine disinfection byproduct of diazepam affects nervous system function and possesses gender-related difference in zebrafish.  ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY,      [PMID:35490575] [10.1016/j.ecoenv.2022.113568]
3. Xiaoke Zheng, Hanyu Yang, Lan Qin, Siqian Wang, Lei Xie, Lu Yang, Weimin Kong, Liang Zhu, Li Liu, Xiaodong Liu.  (2021)  Bile Duct Ligation Upregulates Expression and Function of L-Amino Acid Transporter 1 at Blood–Brain Barrier of Rats via Activation of Aryl Hydrocarbon Receptor by Bilirubin.  Biomedicines,  9  (10): (1320).  [PMID:34680437] [10.3390/biomedicines9101320]
4. Ziming Zheng, Yu Zhang, Yuxuan Liu, Jinglin Wang, Zheng Cui, Xianglin Pan, Yan Liu, Wenqi Tang, Kaiping Wang.  (2020)  Metabolic degradation of lentinan in liver mediated by CYP450 enzymes and epoxide hydrolase.  CARBOHYDRATE POLYMERS,      [PMID:33279005] [10.1016/j.carbpol.2020.117255]
5. Bayarmaa Khadankhuu, Yuxiang Fei, Dan Xu, Yingchao Li, Kai Hou, Fengyang Li, Weirong Fang, Xijing Chen, Yunman Li.  (2019)  Pharmacokinetics and pharmacodynamics analysis of XQ-1H and its combination therapy with clopidogrel on cerebral ischemic reperfusion injury in rats.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:31735472] [10.1016/j.jpba.2019.112975]
6. Xu Mao, Jian Wang, Qian Wang, Lan Yang, Yilin Li, Hao Lin, Ying Peng, Jiang Zheng.  (2019)  Nitidine Chloride–Induced CYP1 Enzyme Inhibition and Alteration of Estradiol Metabolism.  DRUG METABOLISM AND DISPOSITION,  47  (8): (919-927).  [PMID:31147316] [10.1124/dmd.119.086892]
7. Danyi Lu, Zhiguo Ma, Tianpeng Zhang, Xingwang Zhang, Baojian Wu.  (2015)  Metabolism of the anthelmintic drug niclosamide by cytochrome P450 enzymes and UDP-glucuronosyltransferases: metabolite elucidation and main contributions from CYP1A2 and UGT1A1.  XENOBIOTICA,      [PMID:26068521] [10.3109/00498254.2015.1047812]
8. Lili Wu, Wanping Zhong, Junjin Liu, Weichao Han, Shilong Zhong, Qiang Wei, Shuwen Liu, Lan Tang.  (2015)  Human microsomal cyttrochrome P450-mediated reduction of oxysophocarpine, an active and highly toxic constituent derived from Sophora flavescens species, and its intestinal absorption and metabolism in rat.  FITOTERAPIA,      [PMID:26045316] [10.1016/j.fitote.2015.05.021]
9. Baofu Xie, Yue Liu, Chunhong Chen, Tony Velkov, Shusheng Tang, Jianzhong Shen, Chongshan Dai.  (2024)  Colistin Induces Oxidative Stress and Apoptotic Cell Death through the Activation of the AhR/CYP1A1 Pathway in PC12 Cells.  Antioxidants,  13  (7): (827).  [PMID:39061896] [10.3390/antiox13070827]
10. Pinzheng Li, Hengbin Zhang, Yingchun Chen, Shuanghui Lu, Huidi Jiang, Su Zeng, Hui Zhou.  (2025)  CYP-mediated metabolic divergence underpins oxoglaucine selectivity: Detoxification in healthy hepatocytes versus mitochondrial apoptosis in hepatocellular carcinoma.  TOXICOLOGY IN VITRO,      [PMID:41173113] [10.1016/j.tiv.2025.106170]
11. Feifei Zhao, Yizhen Zhu, Lingxiang Mao, Honghao Huang, Wei Wei, Qiangcheng Deng, Youzhi Tang, Ning Han, Zhenling Zeng.  (2025)  Antimicrobial Activity, Preliminary Safety, and Pharmacokinetics Assessment of 2–3: A Pleuromutilin-Derived Compound.  ACS Infectious Diseases,      [PMID:41332299] [10.1021/acsinfecdis.5c00727]
12. Lili Wu, Siyu Chen, Qiyuan Yang, Xing Li, Lingyan Liu, Shengjun Ji, Shuaiyuan Tang, Sihui Zhang, Yan Wang, Runzhi Chen, Zhikun Zhan.  (2026)  Cytochrome P450-Mediated Detoxification and NF-κB/NLRP3 Pathway-Driven Hepatotoxicity of Emodin: Multiomics and laboratory evidence.  CHEMICO-BIOLOGICAL INTERACTIONS,      [PMID:41579920] [10.1016/j.cbi.2026.111934]
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