Escopoletina - ≥98% , CAS No.92-61-5

CAS: 92-61-5 Cat. No.: S100946 Peso molecular: 192.17 Beilstein Registry Number: 156296 Número EC: 202-171-9 PubChem CID: 5280460

GRADE & PURITY ≥98%

Synonyms

AKOS000277133 | Escopoletina | STL570289 | 6-O-Metilesculetina | 7-hidroxi 6-metoxi cumarina | S0367 | 7-Hidroxi-6-metoxi-2H-1-benzopiran-2-ona | IDI1_000720 | Escopoletina, >=99% | Escopoletol | TNP00096 | DivK1c_000720 | HMS1571A05 | Prestwick3_000962 |

Storage

Room temperature

Shipped In

Normal

Specifications

Sinónimos

AKOS000277133 | Escopoletina | STL570289 | 6-O-Metilesculetina | 7-hidroxi 6-metoxi cumarina | S0367 | 7-Hidroxi-6-metoxi-2H-1-benzopiran-2-ona | IDI1_000720 | Escopoletina, >=99% | Escopoletol | TNP00096 | DivK1c_000720 | HMS1571A05 | Prestwick3_000962 |

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

Colorante que puede utilizarse para detectar la liberación de especies reactivas de oxígeno durante el estallido oxidativo; eliminador de peroxinitrito; inhibidor de la acetilcolinesterasa.La escopoletina aumenta significativamente la actividad de la lipo

Condiciones de almacenamiento de almacenamiento

Room temperature

Enviado en

Normal

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 504763304
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763304
• Sonrisas canónicas: COC1=C(C=C2C(=C1)C=CC(=O)O2)O
• IUPAC Name: 7-hydroxy-6-methoxychromen-2-one
• InChIKey: RODXRVNMMDRFIK-UHFFFAOYSA-N
• INCHI: 1S/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3
• Isómeros SMILES: COC1=C(C=C2C(=C1)C=CC(=O)O2)O
• WGK Alemania: 2
• RTECS: GN6930000
• PubChem CID: 5280460
• Peso molecular: 192.17
• Beilstein: 156296

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Clase Coumarins and derivatives
      • Subclass Hydroxycoumarins

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: Coumarins and derivatives
• Subclass: Hydroxycoumarins
• Intermediate Tree Nodes: Not available
• Direct Parent: 7-hydroxycoumarins
• Alternative Parents: 1-benzopyrans Anisoles Pyranones and derivatives Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Heteroaromatic compounds Lactones Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 7-hydroxycoumarin - Benzopyran - 1-benzopyran - Anisole - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Lactone - Oxacycle - Ether - Organoheterocyclic compound - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
• External Descriptors: a small molecule

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)

CA9 Tclin Carbonic anhydrase 9 (1 Activities)

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CA2 Tclin Carbonic anhydrase II (17698 Activities)

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ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

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TYR Tclin Tyrosinase (717 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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ACHE Tclin Acetylcholinesterase (18204 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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XDH Tclin Xanthine dehydrogenase (1038 Activities)

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AKR1B1 Tclin Aldose reductase (1404 Activities)

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CA1 Tclin Carbonic anhydrase I (13240 Activities)

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GLA Tclin Alpha-galactosidase A (5444 Activities)

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GBA1 Tclin Beta-glucocerebrosidase (14647 Activities)

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GAA Tclin Lysosomal alpha-glucosidase (35701 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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SORD Tchem Sorbitol dehydrogenase (133 Activities)

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CASP1 Tchem Caspase-1 (6235 Activities)

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GAPDH Tchem Glyceraldehyde-3-phosphate dehydrogenase liver (1284 Activities)

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ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

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CASP7 Tchem Caspase-7 (3146 Activities)

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CA12 Tclin Carbonic anhydrase XII (6231 Activities)

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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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UGT1A4 Tbio UDP-glucuronosyltransferase 1A4 (288 Activities)

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PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)

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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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CA9 Tclin Carbonic anhydrase IX (8255 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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A498 (42825 Activities)

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ACHN (49357 Activities)

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BXPC-3 (2997 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DLD-1 (17511 Activities)

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DMS-273 (14108 Activities)

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DU-145 (51482 Activities)

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HCT-8 (3484 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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K562 (73714 Activities)

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KM12 (47707 Activities)

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LoVo (4724 Activities)

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M14 (47487 Activities)

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MCF-10A (2462 Activities)

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MCF7 (126967 Activities)

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MKN-45 (2102 Activities)

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MOLT-4 (49676 Activities)

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OVCAR-3 (48710 Activities)

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Objetivos asociados (no humanos)

Ca7 Carbonic anhydrase VII (3 Activities)

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Cruzipain (33337 Activities)

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Ca13 Carbonic anhydrase XIII (322 Activities)

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Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

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Helicobacter pylori (3113 Activities)

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Agrobacterium tumefaciens (620 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Micrococcus luteus (7463 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Aspergillus flavus (8875 Activities)

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Aspergillus niger (16508 Activities)

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Mycobacterium avium (4587 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Enterococcus faecalis (29875 Activities)

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Mycolicibacterium smegmatis (8003 Activities)

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Aspergillus fumigatus (16427 Activities)

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Leishmania infantum (5912 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Leishmania amazonensis (3813 Activities)

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Leishmania braziliensis (1091 Activities)

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Artemia (698 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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Trypanosoma brucei rhodesiense (7991 Activities)

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CCRF S-180 (1031 Activities)

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CHO (4503 Activities)

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L1210 (27553 Activities)

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P388 (20296 Activities)

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P388/ADR (1216 Activities)

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RAW264.7 (28094 Activities)

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BV-2 (3710 Activities)

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L6 (7924 Activities)

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lef Anthrax lethal factor (7585 Activities)

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Fusarium verticillioides (912 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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BCHE Cholinesterase (8742 Activities)

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Fusarium (166 Activities)

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Fusarium incarnatum (10 Activities)

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Aorta (2975 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

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FTL Ferritin light chain (43324 Activities)

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Mesenteric artery (116 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Slightly soluble in water; Soluble in Chloroform
• Punto de fusión (°C): 200-207°C
• Peso molecular: 192.170 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 192.042 Da
• Monoisotopic Mass: 192.042 Da
• Topological Polar Surface Area: 55.800 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 261.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Ying-Hui He, Xiao-Fei Shang, Hai-Xin Li, An-Ping Li, Chen Tang, Bao-Qi Zhang, Zhi-Jun Zhang, Rui Wang, Yue Ma, Sha-Sha Du, Yong-Mei Hu, Tian-Lin Wu, Wen-Bin Zhao, Cheng-Jie Yang, Ying-Qian Liu.  (2021)  Antifungal Activity and Action Mechanism Study of Coumarins from Cnidium monnieri Fruit and Structurally Related Compounds.  CHEMISTRY & BIODIVERSITY,  18  (12): (e2100633).  [PMID:34643056] [10.1002/cbdv.202100633]

2. Feng Li, Jing Li, Jie Zhang, Lili Gao, Xuefeng Long, Yiping Hu, Shuwen Li, Jun Jin, Jiantai Ma.  (2018)  NiO Nanoparticles Anchored on Phosphorus-Doped α-Fe2O3 Nanoarrays: An Efficient Hole Extraction p–n Heterojunction Photoanode for Water Oxidation.  ChemSusChem,  11  (13): (2156-2164).  [PMID:29768719] [10.1002/cssc.201800571]

3. Yaru Li, Zhongmin Liu, Yongchuan Wu, Jitao Chen, Jingyu Zhao, Fengmin Jin, Ping Na.  (2017)  Carbon dots-TiO2 nanosheets composites for photoreduction of Cr(VI) under sunlight illumination: Favorable role of carbon dots.  APPLIED CATALYSIS B-ENVIRONMENTAL,      [PMID:] [10.1016/j.apcatb.2017.10.023]

4. Qiqi Wu, Zhiwei Lin, Haibao Zhu, Chengzhu Ni, Meilan Chen.  (2017)  Simultaneous determination of phytochemicals and low-weight organic acids in Sophora japonica bud and premium noni juice through column-switching liquid chromatography connected with ion chromatography system.  JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES,      [PMID:] [10.1080/10826076.2017.1368025]

5. Qi Sun, Jiajin Zhu, Feiwei Cao, Fengjia Chen.  (2017)  Anti-inflammatory properties of extracts from Chimonanthus nitens Oliv. leaf.  PLoS One,  12  (7): (e0181094).  [PMID:28700722] [10.1371/journal.pone.0181094]

6. Li Wang, Hai-Long Wu, Xiao-Li Yin, Yong Hu, Hui-Wen Gu, Ru-Qin Yu.  (2016)  Simultaneous determination of umbelliferone and scopoletin in Tibetan medicine Saussurea laniceps and traditional Chinese medicine Radix angelicae pubescentis using excitation-emission matrix fluorescence coupled with second-order calibration method.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:27423108] [10.1016/j.saa.2016.07.018]

7. Yang Wenjuan, Tang Sidi, Xu Rubing, Zhang Lu, Zhou Zihao, Yang Yong, Li Yanyan, Xiang Haibo.  (2024)  LC-MS based metabolomics identification of natural metabolites against Fusarium oxysporum.  Frontiers in Plant Science,      [PMID:39290733] [10.3389/fpls.2024.1435963]

8. Liang Luo, Zizhe Li, Qiang Li, Qiyuan Zhao, Xiaonan Wang, Ghulam Mujtaba Mari, Jianzhong Shen, Xuezhi Yu, Zhanhui Wang, Yantong Pan, Jijun Kang.  (2025)  Ratiometric fluorescence immunoassay based on PtPdRu trimetallic nanozyme with enhanced oxidase-like activity for sensitive detection of xylazine.  FOOD CHEMISTRY,      [PMID:40651137] [10.1016/j.foodchem.2025.145442]

9. Junjie Wang, Pengming Yang, Shuai Tu, Weihong Zhong.  (2025)  De Novo Biosynthesis of Scopoletin from Glucose by Engineered Saccharomyces cerevisiae.  BIOCHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.bej.2025.109934]