4-Hydroxycoumarin (BioDeep_00000279086)

Main id: BioDeep_00000000445

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


4-Hydroxy Coumarin;4-Coumarinol;4-Hydroxy-2H-chromen-2-one

化学式: C9H6O3 (162.0317)
中文名称: 4-羟基香豆素, 4-羟基香豆精
谱图信息: 最多检出来源 not specific(not specific) 0%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

4-Hydroxycoumarin. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/4-hydroxycoumarin (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000279086). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=CC=C2C(=C1)C(=CC(=O)O2)O
InChI: InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H

描述信息

4-hydroxycoumarin is a hydroxycoumarin that is coumarin in which the hydrogen at position 4 is replaced by a hydroxy group. It is a conjugate acid of a 4-hydroxycoumarin(1-).
4-Hydroxycoumarin is a natural product found in Vitis vinifera, Ruta graveolens, and Apis cerana with data available.
A hydroxycoumarin that is coumarin in which the hydrogen at position 4 is replaced by a hydroxy group.
D006401 - Hematologic Agents > D000925 - Anticoagulants > D015110 - 4-Hydroxycoumarins
4-hydroxycoumarin is an important fungal metabolite from the precursor coumarin, and its production leads to further fermentative production of the natural anticoagulant dicoumarol. 4-Hydroxy-2H-1-benzopyran-2-one is found in beer and grape wine.
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2338
INTERNAL_ID 2338; CONFIDENCE Reference Standard (Level 1)
4-Hydroxycoumarin, a coumarin derivative, is one of the most versatile heterocyclic scaffolds and is frequently applied in the synthesis of various organic compounds. 4-Hydroxycoumarin possesses both electrophilic and nucleophilic properties. 4-Hydroxycoumarin derivatives are employed as the anticoagulant, antibacterial, antifungal, antiviral, antitumor, antiprotozoal, insecticidal, antimycobacterial, antimutagenic, antioxidant, anti-inflammatory agents, HIV protease inhibitors and tyrosine kinase inhibitors[1].
4-Hydroxycoumarin, a coumarin derivative, is one of the most versatile heterocyclic scaffolds and is frequently applied in the synthesis of various organic compounds. 4-Hydroxycoumarin possesses both electrophilic and nucleophilic properties. 4-Hydroxycoumarin derivatives are employed as the anticoagulant, antibacterial, antifungal, antiviral, antitumor, antiprotozoal, insecticidal, antimycobacterial, antimutagenic, antioxidant, anti-inflammatory agents, HIV protease inhibitors and tyrosine kinase inhibitors[1].

同义名列表

44 个代谢物同义名

4-Hydroxy Coumarin;4-Coumarinol;4-Hydroxy-2H-chromen-2-one; InChI=1/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10; 4-Hydroxy-2H-1-benzopyran-2-one (4-Hydroxycoumarin); 4-Hydroxycoumarin, Vetec(TM) reagent grade, 98\\%; 4-HYDROXY-1-BENZOPYRAN-2-ONE; 4-HYDROXYCOUMARIN; 5-18-01-00378 (Beilstein Handbook Reference); WARFARIN SODIUM IMPURITY B [EP IMPURITY]; 4H-1-Benzopyran-4-one, 2-hydroxy-; 2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-; 4-HYDROXYCOUMARIN [USP IMPURITY]; 4-hydroxy-2H-benzo[b]pyran-2-one; 4-Hydroxy-2H-1-benzopyran-2-one; 2-Hydroxy-4H-1-benzopyran-4-one; 4-hydroxy-2-oxo-2H-1-benzopyran; 4-HYDROXY-1-BENZOPYRAN-2-ONE; 4-Hydroxy-2H-chromen-2-one #; 4-Hydroxy-2H-chromen-2-one; 4-Hydroxy-chromen-2-one; 4-Hydroxycoumarin, 98\\%; 4-hydroxychromen-2-one; 4-hydroxy-2-chromenone; 4-Monohydroxycoumarin; Coumarin, 4-hydroxy-; 4-hydroxyl coumarin; 4- Hydroxycoumarin; 4-hydroxy-coumarin; Benzotetronic acid; 4-Hydroxy coumarin; 4-Hydroxycoumarin; 2-Hydroxychromone; 4-hyroxycoumarin; WLN: T66 BOVJ EQ; 4hydroxycoumarin; hydroxychromone; 4-OH coumarin; MEGxm0_000452; ACon1_001952; 4-Coumarinol; ICCB4_000134; NCI60_000453; AI3-52393; 4HC; \u03b1\uff0dionone; 4-Hydroxycoumarin



数据库引用编号

39 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

29 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 12 ADRM1, BCL2, BECN1, CASP3, CDH2, CYP1A1, CYP2C9, PKM, PTGS2, RAC1, RPSA, TYR
Golgi apparatus, trans-Golgi network membrane 1 BECN1
Peripheral membrane protein 4 ACHE, BECN1, CYP1A1, PTGS2
Endosome membrane 1 BECN1
Endoplasmic reticulum membrane 7 BCL2, BECN1, CYP1A1, CYP2C9, PTGS2, RAC1, VKORC1
Mitochondrion membrane 1 BECN1
Cytoplasmic vesicle, autophagosome 1 BECN1
Nucleus 8 ACHE, ADRM1, BCL2, BECN1, CASP3, PKM, RAC1, RPSA
autophagosome 1 BECN1
cytosol 9 ADRM1, BCL2, BECN1, CASP3, LIPE, PKM, PXN, RAC1, RPSA
dendrite 2 BECN1, RAC1
mitochondrial membrane 1 BECN1
nuclear body 1 BECN1
phagocytic vesicle 1 BECN1
phosphatidylinositol 3-kinase complex, class III 1 BECN1
trans-Golgi network 2 BECN1, RAC1
nucleoplasm 3 ADRM1, CASP3, RPSA
Cell membrane 5 ACHE, CDH2, LIPE, RAC1, RPSA
Lipid-anchor 1 RAC1
Cytoplasmic side 1 RAC1
lamellipodium 3 CDH2, PXN, RAC1
ruffle membrane 1 RAC1
Multi-pass membrane protein 1 VKORC1
Synapse 2 ACHE, RAC1
cell cortex 2 PXN, RAC1
cell junction 1 CDH2
cell surface 2 ACHE, CDH2
glutamatergic synapse 2 CASP3, RAC1
Golgi apparatus 1 ACHE
mitochondrial inner membrane 1 CYP1A1
neuromuscular junction 1 ACHE
neuronal cell body 1 CASP3
postsynapse 1 RAC1
sarcolemma 1 CDH2
Cytoplasm, cytosol 1 LIPE
Lysosome 1 TYR
endosome 1 BECN1
plasma membrane 10 ACHE, ADRM1, BCHE, BTC, CDH2, CYP2C9, F7, PXN, RAC1, RPSA
Membrane 7 ACHE, BCL2, BTC, CDH2, LIPE, RAC1, RPSA
apical plasma membrane 1 CDH2
basolateral plasma membrane 1 CDH2
caveola 2 LIPE, PTGS2
extracellular exosome 3 PKM, RAC1, RPSA
endoplasmic reticulum 4 BCL2, BECN1, PTGS2, VKORC1
extracellular space 4 ACHE, BCHE, BTC, F7
perinuclear region of cytoplasm 2 ACHE, TYR
adherens junction 1 CDH2
apicolateral plasma membrane 1 CDH2
intercalated disc 1 CDH2
mitochondrion 3 BCL2, CYP1A1, PKM
protein-containing complex 2 BCL2, PTGS2
intracellular membrane-bounded organelle 3 CYP1A1, CYP2C9, TYR
Microsome membrane 3 CYP1A1, CYP2C9, PTGS2
postsynaptic density 2 CASP3, CDH2
Single-pass type I membrane protein 2 CDH2, TYR
Secreted 4 ACHE, BCHE, F7, RAC1
extracellular region 6 ACHE, BCHE, BTC, F7, PKM, RAC1
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
Extracellular side 1 ACHE
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
Extracellular vesicle 1 PKM
dendritic spine 1 RAC1
cytoplasmic vesicle 1 RAC1
nucleolus 1 PNMA2
Melanosome membrane 1 TYR
apical part of cell 1 CDH2
cell-cell junction 2 CDH2, PXN
Golgi-associated vesicle 1 TYR
vesicle 2 F7, PKM
presynaptic active zone membrane 1 CDH2
Cell membrane, sarcolemma 1 CDH2
Cell projection, lamellipodium 1 RAC1
Mitochondrion inner membrane 1 CYP1A1
pore complex 1 BCL2
Cell junction, focal adhesion 1 PXN
Cytoplasm, cytoskeleton 1 PXN
focal adhesion 3 CDH2, PXN, RAC1
Cell junction, adherens junction 1 CDH2
basement membrane 1 ACHE
collagen-containing extracellular matrix 3 CDH2, F7, PKM
fascia adherens 1 CDH2
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 2 CDH2, PTGS2
cilium 1 PKM
microtubule associated complex 1 PXN
cytoskeleton 2 PXN, RAC1
cytoplasmic ribonucleoprotein granule 1 RAC1
Nucleus, nucleolus 1 PNMA2
Cytoplasm, cell cortex 1 PXN
blood microparticle 1 BCHE
Lipid-anchor, GPI-anchor 1 ACHE
Recycling endosome membrane 1 RAC1
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
phagophore assembly site 1 BECN1
phosphatidylinositol 3-kinase complex, class III, type I 1 BECN1
phosphatidylinositol 3-kinase complex, class III, type II 1 BECN1
Cell projection, dendrite 1 RAC1
Melanosome 2 RAC1, TYR
side of membrane 1 ACHE
myelin sheath 1 BCL2
stress fiber 1 PXN
plasma membrane raft 1 CDH2
ficolin-1-rich granule lumen 1 PKM
proteasome complex 1 ADRM1
proteasome regulatory particle, lid subcomplex 1 ADRM1
secretory granule lumen 1 PKM
secretory granule membrane 1 RAC1
Golgi lumen 1 F7
endoplasmic reticulum lumen 4 BCHE, CDH2, F7, PTGS2
nuclear envelope lumen 1 BCHE
clathrin-coated endocytic vesicle membrane 1 BTC
synaptic cleft 1 ACHE
ficolin-1-rich granule membrane 1 RAC1
death-inducing signaling complex 1 CASP3
postsynaptic specialization membrane 1 CDH2
Rough endoplasmic reticulum 1 PKM
Cell junction, desmosome 1 CDH2
desmosome 1 CDH2
cytosolic ribosome 1 RPSA
catenin complex 1 CDH2
NADPH oxidase complex 1 RAC1
cytosolic small ribosomal subunit 1 RPSA
serine-type peptidase complex 1 F7
BAD-BCL-2 complex 1 BCL2
[Isoform M2]: Cytoplasm 1 PKM
[Isoform M1]: Cytoplasm 1 PKM
[Isoform H]: Cell membrane 1 ACHE
cytoplasmic side of mitochondrial outer membrane 1 BECN1
small ribosomal subunit 1 RPSA
[Beclin-1-C 35 kDa]: Mitochondrion 1 BECN1
[Beclin-1-C 37 kDa]: Mitochondrion 1 BECN1


文献列表

  • Nadia Taïbi, Qosay Ali Al-Balas, Nadjia Bekari, Oualid Talhi, Ghazi Ahmad Al Jabal, Yasmine Benali, Rachid Ameraoui, Mohamed Hadjadj, Amina Taïbi, Zahra Mouna Boutaiba, Mohamed Abou-Mustapha, Farida Khammar, Fayçal Dergal, Ridha Hassaine, Leila Boukenna, Khaldoun Bachari, Artur Manuel Soares Silva. Molecular docking and dynamic studies of a potential therapeutic target inhibiting glyoxalase system: Metabolic action of the 3, 3 '- [3- (5-chloro-2-hydroxyphenyl) -3-oxopropane-1, 1-diyl] - Bis-4-hydroxycoumarin leads overexpression of the intracellular level of methylglyoxal and induction of a pro-apoptotic phenomenon in a hepatocellular carcinoma model. Chemico-biological interactions. 2021 Aug; 345(?):109511. doi: 10.1016/j.cbi.2021.109511. [PMID: 33989593]
  • Joanna Sumorek-Wiadro, Adrian Zając, Ewa Langner, Krystyna Skalicka-Woźniak, Aleksandra Maciejczyk, Wojciech Rzeski, Joanna Jakubowicz-Gil. Antiglioma Potential of Coumarins Combined with Sorafenib. Molecules (Basel, Switzerland). 2020 Nov; 25(21):. doi: 10.3390/molecules25215192. [PMID: 33171577]
  • Hajar Golshadi Ghalehshahi, Saeed Balalaie, Atousa Aliahmadi, Roya Moghimi. Synthesis of 4-N-α-coumaryl amino acids and investigation of their antioxidant, antimicrobial activities and fluorescence spectra. Amino acids. 2018 Oct; 50(10):1461-1470. doi: 10.1007/s00726-018-2624-5. [PMID: 30046883]
  • Yang Gao, Guo-Ning Zhang, Juxian Wang, Xiaoguang Bai, Yiliang Li, Yucheng Wang. One-Pot Syntesis of 3-Functionalized 4-Hydroxycoumarin under Catalyst-Free Conditions. Molecules (Basel, Switzerland). 2018 Jan; 23(1):. doi: 10.3390/molecules23010235. [PMID: 29361771]
  • Zheng Hou, Ying Zhou, Jing Li, Xinlei Zhang, Xin Shi, Xiaoyan Xue, Zhi Li, Bo Ma, Yukun Wang, Mingkai Li, Xiaoxing Luo. Selective in vivo and in vitro activities of 3,3'-4-nitrobenzylidene-bis-4-hydroxycoumarin against methicillin-resistant Staphylococcus aureus by inhibition of DNA polymerase III. Scientific reports. 2015 Sep; 5(?):13637. doi: 10.1038/srep13637. [PMID: 26323712]
  • Milan Mladenović, Mirjana Mihailović, Desanka Bogojević, Nenad Vuković, Slobodan Sukdolak, Sanja Matić, Neda Nićiforović, Vladimir Mihailović, Pavle Mašković, Miroslav M Vrvić, Slavica Solujić. Biochemical and pharmacological evaluation of 4-hydroxychromen-2-ones bearing polar C-3 substituents as anticoagulants. European journal of medicinal chemistry. 2012 Aug; 54(?):144-58. doi: 10.1016/j.ejmech.2012.04.036. [PMID: 22633008]
  • Chung-Yi Chen, Kuo-Chen Cheng, Andy Y Chang, Ying-Ting Lin, You-Cheng Hseu, Hui-Min Wang. 10-Shogaol, an antioxidant from Zingiber officinale for skin cell proliferation and migration enhancer. International journal of molecular sciences. 2012; 13(2):1762-1777. doi: 10.3390/ijms13021762. [PMID: 22408422]
  • Alinanuswe S Mwakaboko, Binne Zwanenburg. Single step synthesis of strigolactone analogues from cyclic keto enols, germination stimulants for seeds of parasitic weeds. Bioorganic & medicinal chemistry. 2011 Aug; 19(16):5006-11. doi: 10.1016/j.bmc.2011.06.057. [PMID: 21757362]
  • Jae-chul Jung, Hyung-in Moon. Larvicidal activity of 4-hydroxycoumarin derivatives against Aedes aegypti. Pharmaceutical biology. 2011 Feb; 49(2):190-3. doi: 10.3109/13880209.2010.507769. [PMID: 21043993]
  • Sílvia Helena Cestari, Jairo Kennup Bastos, Luiz Claudio Di Stasi. Intestinal Anti-Inflammatory Activity of Baccharis dracunculifolia in the Trinitrobenzenesulphonic Acid Model of Rat Colitis. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):524349. doi: 10.1093/ecam/nep081. [PMID: 19592480]
  • Milan Mladenović, Mirjana Mihailović, Desanka Bogojević, Sanja Matić, Neda Nićiforović, Vladimir Mihailović, Nenad Vuković, Slobodan Sukdolak, Slavica Solujić. In vitro antioxidant activity of selected 4-hydroxy-chromene-2-one derivatives-SAR, QSAR and DFT studies. International journal of molecular sciences. 2011; 12(5):2822-41. doi: 10.3390/ijms12052822. [PMID: 21686153]
  • Amin Al-Shami, Kanchan G Jhaver, Peter Vogel, Carrie Wilkins, Juliane Humphries, John J Davis, Nianhua Xu, David G Potter, Brenda Gerhardt, Robert Mullinax, Cynthia R Shirley, Stephen J Anderson, Tamas Oravecz. Regulators of the proteasome pathway, Uch37 and Rpn13, play distinct roles in mouse development. PloS one. 2010 Oct; 5(10):e13654. doi: 10.1371/journal.pone.0013654. [PMID: 21048919]
  • Vessela D Kancheva, Petya V Boranova, Jordan T Nechev, Ilia I Manolov. Structure-activity relationships of new 4-hydroxy bis-coumarins as radical scavengers and chain-breaking antioxidants. Biochimie. 2010 Sep; 92(9):1138-46. doi: 10.1016/j.biochi.2010.02.033. [PMID: 20211681]
  • Nohemí Salinas-Jazmín, Marisol de la Fuente, Ruth Jaimez, Mayra Pérez-Tapia, Armando Pérez-Torres, Marco A Velasco-Velázquez. Antimetastatic, antineoplastic, and toxic effects of 4-hydroxycoumarin in a preclinical mouse melanoma model. Cancer chemotherapy and pharmacology. 2010 Apr; 65(5):931-40. doi: 10.1007/s00280-009-1100-z. [PMID: 19690859]
  • K S Joseph, Annette C Moser, Sara B G Basiaga, John E Schiel, David S Hage. Evaluation of alternatives to warfarin as probes for Sudlow site I of human serum albumin: characterization by high-performance affinity chromatography. Journal of chromatography. A. 2009 Apr; 1216(16):3492-500. doi: 10.1016/j.chroma.2008.09.080. [PMID: 18926542]
  • Marcel Albrecht, Oliver Schneider, Andreas Schmidt. Redox active donor-substituted punicin derivatives. Organic & biomolecular chemistry. 2009 Apr; 7(7):1445-53. doi: 10.1039/b822353j. [PMID: 19300831]
  • Shujiang Tu, Shanshan Wu, Shu Yan, Wenjuan Hao, Xiaohong Zhang, Xudong Cao, Zhengguo Han, Bo Jiang, Feng Shi, Min Xia, Jianfeng Zhou. Design and microwave-assisted synthesis of naphtho[2,3-f]quinoline derivatives and their luminescent properties. Journal of combinatorial chemistry. 2009 Mar; 11(2):239-42. doi: 10.1021/cc800094m. [PMID: 19115830]
  • Krzysztof Wójtowicz. Comparison of the effect of 4-hydroxycoumarin and umbelliferone on the phase transition of dipalmitoylphosphatidylcholine (DPPC) bilayers. Pharmacological reports : PR. 2008 Jul; 60(4):555-60. doi: . [PMID: 18799825]
  • Carlos L Céspedes, J Guillermo Avila, Andrés Martínez, Blanca Serrato, José C Calderón-Mugica, Rafael Salgado-Garciglia. Antifungal and antibacterial activities of Mexican tarragon (Tagetes lucida). Journal of agricultural and food chemistry. 2006 May; 54(10):3521-7. doi: 10.1021/jf053071w. [PMID: 19127719]
  • Subbiah Deepa, Ashok K Mishra. Fluorescence spectroscopic study of serum albumin-bromadiolone interaction: fluorimetric determination of bromadiolone. Journal of pharmaceutical and biomedical analysis. 2005 Jul; 38(3):556-63. doi: 10.1016/j.jpba.2005.01.023. [PMID: 15925260]
  • Jian-Tao He, Zhi-Hong Shi, Jin Yan, Mei-Ping Zhao, Zhen-Quan Guo, Wen-Bao Chang. Biotin-avidin amplified enzyme-linked immunosorbent assay for determination of isoflavone daidzein. Talanta. 2005 Feb; 65(3):621-6. doi: 10.1016/j.talanta.2004.07.027. [PMID: 18969844]
  • Hideki Kanho, Sayaka Yaoya, Tomio Itani, Takahisa Nakane, Nobuo Kawahara, Yoichi Takase, Kazuo Masuda, Masanori Kuroyanagi. Glucosylation of phenolic compounds by Pharbitis nil hairy roots: I. Glucosylation of coumarin and flavone derivatives. Bioscience, biotechnology, and biochemistry. 2004 Oct; 68(10):2032-9. doi: 10.1271/bbb.68.2032. [PMID: 15502347]
  • Anna Oliva, Kumudini M Meepagala, David E Wedge, Dewayne Harries, Amber L Hale, Giovanni Aliotta, Stephen O Duke. Natural fungicides from Ruta graveolens L. leaves, including a new quinolone alkaloid. Journal of agricultural and food chemistry. 2003 Feb; 51(4):890-6. doi: 10.1021/jf0259361. [PMID: 12568545]
  • Claudia Bocca, Ludovica Gabriel, Francesca Bozzo, Antonella Miglietta. Microtubule-interacting activity and cytotoxicity of the prenylated coumarin ferulenol. Planta medica. 2002 Dec; 68(12):1135-7. doi: 10.1055/s-2002-36342. [PMID: 12494346]
  • L Vander Elst, S Laurent, H M Bintoma, R N Muller. Albumin-bound MRI contrast agents: the dilemma of the rotational correlation time. Magma (New York, N.Y.). 2001 May; 12(2-3):135-40. doi: 10.1007/bf02668095. [PMID: 11390269]
  • Y Masamoto. [Sensitization and crossreaction of simple coumarins]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2001 Jan; 121(1):97-103. doi: 10.1248/yakushi.121.97. [PMID: 11201168]
  • A M Zatón, J P Villamor. Study of heterocycle rings binding to human serum albumin. Chemico-biological interactions. 2000 Jan; 124(1):1-11. doi: 10.1016/s0009-2797(99)00130-1. [PMID: 10658898]
  • D Lamnaouer. [Anticoagulant activity of coumarins from Ferula communis L]. Therapie. 1999 Nov; 54(6):747-51. doi: ". [PMID: 10709451]
  • H H Maurer, J W Arlt. Detection of 4-hydroxycoumarin anticoagulants and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation. Journal of chromatography. B, Biomedical sciences and applications. 1998 Sep; 714(2):181-95. doi: 10.1016/s0378-4347(98)00243-6. [PMID: 9766858]
  • A M Rao, A Dogan, J F Hatcher, R J Dempsey. Fluorometric assay of nitrite and nitrate in brain tissue after traumatic brain injury and cerebral ischemia. Brain research. 1998 May; 793(1-2):265-70. doi: 10.1016/s0006-8993(98)00183-8. [PMID: 9630667]
  • T Chalermchaikit, L J Felice, M J Murphy. Simultaneous determination of eight anticoagulant rodenticides in blood serum and liver. Journal of analytical toxicology. 1993 Jan; 17(1):56-61. doi: 10.1093/jat/17.1.56. [PMID: 8429630]
  • K Stuhlmeier, G Theyer, G Baumgartner, G J Zlabinger. Synergistic effect of coumarin (1,2 benzopyrone) and endotoxin in the induction of human interleukin-1. Clinical and experimental immunology. 1991 May; 84(2):317-23. doi: 10.1111/j.1365-2249.1991.tb08167.x. [PMID: 2025958]
  • F SALVI. [Histochemical findings after treatment with 3-(1-phenylpropyl)4-hydroxycoumarin; experimental study]. Rivista di anatomia patologica e di oncologia. 1954 Jun; 8(5):711-25. doi: NULL. [PMID: 13237837]
  • S ROSEMAN, H GREEN. A colorimetric method for the determination of dicumarol (3,3'-methylenebis (4-hydroxycoumarin)) in plasma. The Journal of laboratory and clinical medicine. 1951 Feb; 37(2):321-4. doi: NULL. [PMID: 14814360]
  • V GROSSMANN, I M HAIS, B KASALICKY. [Inhibition of serum cholinesterase by certain derivatives of 4-hydroxycoumarin]. Casopis lekaru ceskych. 1950 Apr; 89(17):487-8. doi: . [PMID: 15414533]
  • J AXELROD, J R COOPER, B B BRODIE. Estimation of dicumarol, 3,31-methylenebis (4-hydroxycoumarin) in biological fluids. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1949 Apr; 70(4):693-5. doi: 10.3181/00379727-70-17036. [PMID: 18144836]
  • . . . . doi: . [PMID: 18487633]
  • . . . . doi: . [PMID: 19757094]