创建日期
2005-11-16 15:48:42 UTC
更新日期
2021-10-13 04:27:40 UTC
描述
Maleic acid is a dicarboxylic acid, a molecule with two carboxyl groups. It consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 oC) is also much lower than that of fumaric acid (287 oC). Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. Maleic acid is used in making polyesters for fibre-reinforced laminated moldings and paint vehicles. More specifically it is used in the manufacture of phthalic-type alkyd and polyester resins, surface coatings, copolymers, plasticizers, lubricant additives and agricultural chemicals. It is also found in adhesives and sealants and as a preservative for oils and fats. In the natural world, maleic acid has been identified in ginseng, pineapple, cacao plants, sour cherries and corn. A large number of microbes are able to convert maleic acid to D-malate using the enzyme maleate hydratase (PMID: 1444397).
同义词
1:(Z)-2-Butenedioic acid
2:(Z)-Butenedioic acid
3:cis-1,2-Ethylenedicarboxylic acid
4:cis-But-2-enedioic acid
5:cis-Butenedioic acid
6:H2Male
7:Toxilic acid
8:Maleate
9:(Z)-2-Butenedioate
10:(Z)-Butenedioate
11:cis-1,2-Ethylenedicarboxylate
12:cis-But-2-enedioate
13:cis-Butenedioate
14:Toxilate
15:(2Z)-2-Butenedioate
16:(2Z)-2-Butenedioic acid
17:(2Z)-But-2-enedioate
18:(2Z)-But-2-enedioic acid
19:(2Z)-Butene-2-dioate
20:(2Z)-Butene-2-dioic acid
21:2-Butenedioate
22:2-Butenedioic acid
23:cis-2-Butenedioate
24:cis-2-Butenedioic acid
25:Kyselina maleinova
26:MAE
27:Maleinic acid
28:Malenic acid
29:Malezid CM
30:Scotchbond multipurpose etchant
31:Maleic acid, disodium salt
32:Maleic acid, monocopper (2+) salt
33:Maleic acid, potassium salt
34:Maleic acid, sodium salt
35:Sodium maleate
36:Hydrogen maleate
37:Maleic acid, ammonium salt
38:Maleic acid, calcium salt
39:Maleic acid, iron salt
40:Maleic acid, neodymium salt
41:Maleic acid, dipotassium salt
42:Maleic acid, monoammonium salt
43:Maleic acid, monosodium salt
化学名称
(2Z)-but-2-enedioic acid
代谢物结构字符串
OC(=O)\C=C/C(O)=O
inchi标识符
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
印记键
VZCYOOQTPOCHFL-UPHRSURJSA-N
分类学
description: belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
description:Dicarboxylic acids and derivatives
kingdom:Organic compounds
super_class:Organic acids and derivatives
class:Carboxylic acids and derivatives
sub_class:Dicarboxylic acids and derivatives
molecular_framework:Aliphatic acyclic compounds
1:Carbonyl compounds
2:Carboxylic acids
3:Hydrocarbon derivatives
4:Organic oxides
5:Unsaturated fatty acids
6:Aliphatic acyclic compound
7:Carbonyl group
8:Carboxylic acid
9:Dicarboxylic acid or derivatives
10:Fatty acid
11:Fatty acyl
12:Hydrocarbon derivative
13:Organic oxide
14:Organic oxygen compound
15:Organooxygen compound
16:Unsaturated fatty acid
17:butenedioic acid
本体论
term:Disposition
definition:A concept that describes the origin of a chemical, its location within an organism, or its route of exposure.
parent_id:
level:1
type:parent
term:Route of exposure
definition:A mean by which a chemical agent comes in contact with an organism, either under intended or unintended circumstances.
parent_id:7724
*level:2
type:parent
term:Enteral
definition:Chemical exposure via the alimentary canal (mouth to anus).
parent_id:7743
**level:3
type:parent
term:Ingestion
definition:Chemical exposure facilitated by entry through the mouth.
parent_id:7744
***level:4
type:child
synonym:Digestion
term:Source
definition:Natural or synthetic origin of a chemical.
parent_id:7724
*level:2
type:parent
term:Endogenous
definition:
parent_id:7735
**level:3
type:child
term:Food
definition:
parent_id:7735
**level:3
type:child
term:Biological
definition:A living organism (species or a higher taxonomy rank), in which a chemical can be found.
parent_id:7735
**level:3
type:parent
term:Plant
definition:A living organism belonging to the kingdom plantea. typically, it grows in a permanent site, absorbs water and inorganic substances through its roots, and synthesizes nutrients in its leaves by photosynthesis using the green pigment chlorophyll. examples incude trees, shrubs, herbs, grasses, ferns, and mosses.
parent_id:7736
***level:4
type:parent
synonym:Flora
term:Biological location
definition:The physiological origin within an organism, including anatomical compnents, biofluids and excreta.
parent_id:7724
*level:2
type:parent
term:Tissue and substructures
definition:An anatomical organizational level including multiple cells yet not comprising a complete organ .
parent_id:7725
**level:3
type:parent
term:Muscle
definition:A fibrous soft tissue with the ability to contract to produce force and motion. (nci).
parent_id:7729
***level:4
type:child
term:Organ and components
definition:An anatomical organizational level including multiple tissues or substructures, which enables a common biological function.
parent_id:7725
**level:3
type:parent
term:Spleen
definition:An abdominal organ that is part of the hematopoietic and immune systems. it is composed of the white pulp and the red pulp and is surrounded by a capsule. (nci).
parent_id:7727
***level:4
type:child
term:Prostate
definition:The male reproductive accessory gland that produces prostatic fluid and is located adjacent to or around the urethra distal to the urinary bladder in mammals. (nci).
parent_id:7727
***level:4
type:child
synonym:Prostate gland
term:Pancreas
definition:A digestive organ in the abdomen that has both endocrine and exocrine functions. (nci).
parent_id:7727
***level:4
type:child
term:Biofluid and excreta
definition:A liquid, semi-solid or solid material originating in the body.
parent_id:7725
**level:3
type:parent
term:Feces
definition:The material discharged from the bowel during defecation. It consists of undigested food, intestinal mucus, epithelial cells, and bacteria.
parent_id:7731
***level:4
type:child
synonym:Fecal
synonym:Stool
synonym:Faecal
synonym:Faeces
term:Urine
definition:Excretion in liquid state processed by the kidney.
parent_id:7731
***level:4
type:child
term:Blood
definition:A liquid tissue with the primary function of transporting oxygen and carbon dioxide (nci). it supplies the tissues with nutrients, removes waste products, and contains various components of the immune system defending the body against infection.
parent_id:7731
***level:4
type:child
term:Subcellular
definition:An anatomical organizational level including a component within a biological cell .
parent_id:7725
**level:3
type:parent
term:Cytoplasm
definition:The portion of the cell contained within the plasma membrane but excluding the nucleus.
parent_id:7730
***level:4
type:child
synonym:Cytoplasma
term:Membrane
definition:
parent_id:7730
***level:4
type:child
term:Cell membrane
definition:A cellular compartment that separates a cellВ interiorВ from its exterior.
parent_id:7730
***level:4
type:child
synonym:Cellular membrane
term:Cell and elements
definition:An anatomical organizational level comprising of a single cell (or a fragment in some exceptions). a cell is defined by its type or function. it is the smallest unit of living structure capable of independent existence, composed of a membrane-enclosed mass of protoplasm and containing a nucleus or nucleoid.
parent_id:7725
**level:3
type:parent
term:Extracellular
definition:The space external to the outermost structure of a cell.
parent_id:7732
***level:4
type:child
synonym:Extracellular region
term:Element
definition:
parent_id:7732
***level:4
type:parent
term:Cell
definition:
parent_id:7732
***level:4
type:parent
term:Process
definition:Biological or chemical events, or a series thereof, leading to a known function or end-product.
parent_id:
level:1
type:parent
term:Naturally occurring process
definition:Naturally-occurring molecular events or a series thereof, leading to a known function or end-product.
parent_id:7659
*level:2
type:parent
term:Biological process
definition:Biological or chemical events or a series thereof, leading to a known function or end-product within an organism.
parent_id:7660
**level:3
type:parent
term:Cellular process
definition:A biological process occurring within a cell or its surroundings.
parent_id:7661
***level:4
type:parent
term:Role
definition:The purpose or function assumed by a chemical, either naturally or as intended by humans .
parent_id:
level:1
type:parent
term:Biological role
definition:The biological function of a chemical. the biological role answers the question how a chemical is involved in molecular processes in an organism. this can include biochemical effects of non-endogenous chemicals, which are also assigned an industrial application such as pharmaceuticals. the biological role is limited to cellular levls, and will not include role at system process level, such as a chemical which has a role in a disease.
parent_id:7671
*level:2
type:parent
term:Membrane stabilizer
definition:A chemical substance that supports the formation and maintenance of a structurally-sound and functioning cell or organelle membrane. Phospholipids form a bilayer and maintain the stability of the membrane structure together with proteins, and other lipids (i.e. cholesterol) which further strengthen it and decrease its permeability.
parent_id:7672
**level:3
type:child
synonym:Membrane stability agent
synonym:Membrane integrity agent
term:Energy source
definition:
parent_id:7672
**level:3
type:child
term:Energy storage
definition:A chemical substance which can be utilized for production of energy in the organism.
parent_id:7672
**level:3
type:child
term:Environmental role
definition:A direct or indirect function of chemical product or process which affect the components of the environment.
parent_id:7671
*level:2
type:parent
term:Air pollutant
definition:An airborne chemical substance, natural or synthetic, that is harmful to organisms and the environment. may consist of solid particles, liquid droplets or gases, or combinations of these forms.
parent_id:7692
**level:3
type:child
term:Industrial application
definition:The assumed function of a chemical utilized by human.
parent_id:7671
*level:2
type:parent
term:Surfactant
definition:A chemical substance that has the ability to lower the surface tension of water or to reduce the interfacial tension between two immiscible substances. in the cspa consumer product ingredients dictionary, surfactants are classified on the basis of their ionic characteristics, as amphoteric, anionic, cationic, or nonionic; and functions, which are subdivided into the following major groups: surfactant - cleaning agent, surfactant - conditioning agent, surfactant - emulsifying agent, surfactant - foam booster , surfactant hydrotrop , surfactant - solubility agent, surfactant - suspending agent.
parent_id:7678
**level:3
type:child
synonym:Surface-active agent
term:Emulsifier
definition:Substances that promote the formation and stability of a suspension of fine particles of a liquid in another liquid.
parent_id:7678
**level:3
type:child
term:Pharmaceutical industry
definition:A pharmacologic activity for which a chemical substance is utilized owing to its biological role.
parent_id:7678
**level:3
type:parent
term:Pharmaceutical
definition:
parent_id:7679
***level:4
type:child
实验性质
1:
kind:water_solubility
value:441 mg/mL at 25 °C
source:
2:
kind:logp
value:-0.48
source:SANGSTER (1994)
3:
kind:melting_point
value:130.5 °C
source:
4:
kind:boiling_point
value:355.00 to 356.00 °C. @ 760.00 mm Hg (est)
source:The Good Scents Company Information System
预测性质
1:
kind:logp
value:0.21
source:ALOGPS
2:
kind:logs
value:-0.68
source:ALOGPS
3:
kind:solubility
value:24.1 g/L
source:ALOGPS
4:
kind:logp
value:-0.041
source:ChemAxon
5:
kind:pka_strongest_acidic
value:3.05
source:ChemAxon
6:
kind:iupac
value:(2Z)-but-2-enedioic acid
source:ChemAxon
7:
kind:average_mass
value:116.0722
source:ChemAxon
8:
kind:mono_mass
value:116.010958616
source:ChemAxon
9:
kind:smiles
value:OC(=O)\C=C/C(O)=O
source:ChemAxon
10:
kind:formula
value:C4H4O4
source:ChemAxon
11:
kind:inchi
value:InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
source:ChemAxon
12:
kind:inchikey
value:VZCYOOQTPOCHFL-UPHRSURJSA-N
source:ChemAxon
13:
kind:polar_surface_area
value:74.6
source:ChemAxon
14:
kind:refractivity
value:24.61
source:ChemAxon
15:
kind:polarizability
value:9.19
source:ChemAxon
16:
kind:rotatable_bond_count
value:2
source:ChemAxon
17:
kind:acceptor_count
value:4
source:ChemAxon
18:
kind:donor_count
value:2
source:ChemAxon
19:
kind:physiological_charge
value:-2
source:ChemAxon
20:
kind:formal_charge
value:0
source:ChemAxon
21:
kind:number_of_rings
value:0
source:ChemAxon
22:
kind:bioavailability
value:Yes
source:ChemAxon
23:
kind:rule_of_five
value:Yes
source:ChemAxon
24:
kind:ghose_filter
value:No
source:ChemAxon
25:
kind:veber_rule
value:No
source:ChemAxon
26:
kind:mddr_like_rule
value:No
source:ChemAxon
1:
type:Specdb::NmrTwoD
spectrum_id:984
2:
type:Specdb::NmrTwoD
spectrum_id:1188
3:
type:Specdb::CMs
spectrum_id:415
4:
type:Specdb::CMs
spectrum_id:1036
5:
type:Specdb::CMs
spectrum_id:8094
6:
type:Specdb::CMs
spectrum_id:27693
7:
type:Specdb::CMs
spectrum_id:29705
8:
type:Specdb::CMs
spectrum_id:30138
9:
type:Specdb::CMs
spectrum_id:30617
10:
type:Specdb::CMs
spectrum_id:31050
11:
type:Specdb::CMs
spectrum_id:31936
12:
type:Specdb::CMs
spectrum_id:37339
13:
type:Specdb::CMs
spectrum_id:131405
14:
type:Specdb::CMs
spectrum_id:139139
15:
type:Specdb::NmrOneD
spectrum_id:1144
16:
type:Specdb::NmrOneD
spectrum_id:142710
17:
type:Specdb::NmrOneD
spectrum_id:142711
18:
type:Specdb::NmrOneD
spectrum_id:142712
19:
type:Specdb::NmrOneD
spectrum_id:142713
20:
type:Specdb::NmrOneD
spectrum_id:142714
21:
type:Specdb::NmrOneD
spectrum_id:142715
22:
type:Specdb::NmrOneD
spectrum_id:142716
23:
type:Specdb::NmrOneD
spectrum_id:142717
24:
type:Specdb::NmrOneD
spectrum_id:142718
25:
type:Specdb::NmrOneD
spectrum_id:142719
26:
type:Specdb::NmrOneD
spectrum_id:142720
27:
type:Specdb::NmrOneD
spectrum_id:142721
28:
type:Specdb::NmrOneD
spectrum_id:142722
29:
type:Specdb::NmrOneD
spectrum_id:142723
30:
type:Specdb::NmrOneD
spectrum_id:142724
31:
type:Specdb::NmrOneD
spectrum_id:142725
32:
type:Specdb::NmrOneD
spectrum_id:142726
33:
type:Specdb::NmrOneD
spectrum_id:142727
34:
type:Specdb::NmrOneD
spectrum_id:142728
35:
type:Specdb::NmrOneD
spectrum_id:142729
36:
type:Specdb::MsMs
spectrum_id:280
37:
type:Specdb::MsMs
spectrum_id:281
38:
type:Specdb::MsMs
spectrum_id:282
39:
type:Specdb::MsMs
spectrum_id:3343
40:
type:Specdb::MsMs
spectrum_id:3344
41:
type:Specdb::MsMs
spectrum_id:3345
42:
type:Specdb::MsMs
spectrum_id:3346
43:
type:Specdb::MsMs
spectrum_id:3347
44:
type:Specdb::MsMs
spectrum_id:3348
45:
type:Specdb::MsMs
spectrum_id:3350
46:
type:Specdb::MsMs
spectrum_id:257739
47:
type:Specdb::MsMs
spectrum_id:257740
48:
type:Specdb::MsMs
spectrum_id:257741
49:
type:Specdb::MsMs
spectrum_id:277677
50:
type:Specdb::MsMs
spectrum_id:277678
51:
type:Specdb::MsMs
spectrum_id:277679
52:
type:Specdb::MsMs
spectrum_id:438089
53:
type:Specdb::MsMs
spectrum_id:438090
54:
type:Specdb::MsMs
spectrum_id:438091
55:
type:Specdb::MsMs
spectrum_id:438092
56:
type:Specdb::MsMs
spectrum_id:438093
57:
type:Specdb::MsMs
spectrum_id:439264
58:
type:Specdb::MsMs
spectrum_id:2252760
59:
type:Specdb::MsMs
spectrum_id:2254773
60:
type:Specdb::MsMs
spectrum_id:2255783
生物学性质
1:
cellular:(1):Cytoplasm
cellular:(2):Extracellular
cellular:(3):Membrane
2:
biospecimen:(1):Blood
biospecimen:(2):Feces
biospecimen:(3):Urine
3:
tissue:(1):Fibroblasts
tissue:(2):Neuron
tissue:(3):Pancreas
tissue:(4):Platelet
tissue:(5):Prostate
tissue:(6):Skeletal Muscle
tissue:(7):Spleen
4:
正常浓度
1:
biospecimen:Blood
concentration_value:
concentration_units:
subject_age:
subject_sex:
subject_condition:Normal
2:
biospecimen:Feces
concentration_value:
concentration_units:
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
3:
biospecimen:Feces
concentration_value:
concentration_units:
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
4:
biospecimen:Feces
concentration_value:
concentration_units:
subject_age:Not Specified
subject_sex:Not Specified
subject_condition:Normal
5:
biospecimen:Urine
concentration_value:5.447 +/- 6.8
concentration_units:umol/mmol creatinine
subject_age:Children (1 - 13 years old)
subject_sex:Not Specified
subject_condition:Normal
6:
biospecimen:Urine
concentration_value:10.4
concentration_units:umol/mmol creatinine
subject_age:Newborn (0-30 days old)
subject_sex:Both
subject_condition:Normal
7:
biospecimen:Urine
concentration_value:10.7
concentration_units:umol/mmol creatinine
subject_age:Infant (0-1 year old)
subject_sex:Both
subject_condition:Normal
8:
biospecimen:Urine
concentration_value:0.7
concentration_units:umol/mmol creatinine
subject_age:Children (1-13 years old)
subject_sex:Both
subject_condition:Normal
9:
biospecimen:Urine
concentration_value:0.1
concentration_units:umol/mmol creatinine
subject_age:Children (1-13 years old)
subject_sex:Both
subject_condition:Normal
10:
biospecimen:Urine
concentration_value:0.5
concentration_units:umol/mmol creatinine
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
11:
biospecimen:Urine
concentration_value:0.4 (0.3-0.5)
concentration_units:umol/mmol creatinine
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
12:
biospecimen:Urine
concentration_value:10.7
concentration_units:umol/mmol creatinine
subject_age:Adult (>18 years old)
subject_sex:Not Specified
subject_condition:Normal
13:
biospecimen:Urine
concentration_value:0.1
concentration_units:umol/mmol creatinine
subject_age:Not Specified
subject_sex:Not Specified
subject_condition:Normal
异常浓度
1:
biospecimen:Urine
concentration_value:1.585 +/- 1.123
concentration_units:umol/mmol creatinine
patient_age:Children (1 - 13 years old)
patient_sex:Not Specified
patient_information:Eosinophilic esophagitis
疾病参考
1:
name:Eosinophilic esophagitis
omim_id:610247
[1]:
reference_text:Mordechai, Hien, and David S. Wishart
pubmed_id:
综合参考
Dethloff, Christian; Barbarino, Sergio. Process temperature optimization in the manufacture of maleic acid by the hydrolysis of maleic anhydride. Eur. Pat. Appl. (1998), 7 pp.
蛋白质结合
1:
reference_text:Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6.
pubmed_id:8087979
2:
reference_text:Kotikoski H, Oksala O, Vapaatalo H, Aine E: Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers. Acta Ophthalmol Scand. 2003 Aug;81(4):355-60.
pubmed_id:12859262
3:
reference_text:Herreras JM, Pastor JC, Calonge M, Asensio VM: Ocular surface alteration after long-term treatment with an antiglaucomatous drug. Ophthalmology. 1992 Jul;99(7):1082-8.
pubmed_id:1495787
4:
reference_text:Klose T, Welzel PB, Werner C: Protein adsorption from flowing solutions on pure and maleic acid copolymer modified glass particles. Colloids Surf B Biointerfaces. 2006 Aug 1;51(1):1-9. Epub 2006 May 17.
pubmed_id:16797943
5:
reference_text:Renner L, Pompe T, Salchert K, Werner C: Dynamic alterations of fibronectin layers on copolymer substrates with graded physicochemical characteristics. Langmuir. 2004 Mar 30;20(7):2928-33.
pubmed_id:15835174
6:
reference_text:Gong Z, Lv Y, Huang Y, Zhang Z: Determination of ergometrine maleate by fluorescence detection. Luminescence. 2005 May-Jun;20(3):124-8.
pubmed_id:15924314
7:
reference_text:Goes MF, Sinhoreti MA, Consani S, Silva MA: Morphological effect of the type, concentration and etching time of acid solutions on enamel and dentin surfaces. Braz Dent J. 1998;9(1):3-10.
pubmed_id:9835798
8:
reference_text:Gallagher RM: Menstrual migraine and intermittent ergonovine therapy. Headache. 1989 Jun;29(6):366-7.
pubmed_id:2759844
9:
reference_text:Seki T, Wakabayashi M, Nakagawa T, Imamura M, Tamai T, Nishimura A, Yamashiki N, Okamura A, Inoue K: Hepatic infarction following percutaneous ethanol injection therapy for hepatocellular carcinoma. Eur J Gastroenterol Hepatol. 1998 Nov;10(11):915-8.
pubmed_id:9872612
10:
reference_text:Snider BJ, Moss JL, Revilla FJ, Lee CS, Wheeler VC, Macdonald ME, Choi DW: Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults. Neuroscience. 2003;120(3):617-25.
pubmed_id:12895502
11:
reference_text:Lavit M, Saivin S, Boudra H, Michel F, Martin A, Cahiez G, Labaune JP, Chomard JM, Houin G: Determination of trimebutine and desmethyl-trimebutine in human plasma by HPLC. Arzneimittelforschung. 2000 Jul;50(7):640-4.
pubmed_id:10965422
12:
reference_text:Strasser G, Grabner G: The influence of long-term treatment with timolol on human tear lysozyme albumin content. Graefes Arch Clin Exp Ophthalmol. 1982;218(2):93-5.
pubmed_id:7075967
13:
reference_text:Glazunova OO, Korepanova EA, Efimov VS, Smirnov AI, Vladimirov YuA: A synthetic polycation, a copolymer of 1-vinyl-3-methylimidazole iodide with maleic acid diethyl ester, increases passive ionic permeability in erythrocyte membranes modified by fatty acids. Membr Cell Biol. 1998;12(3):401-9.
pubmed_id:10024972
14:
reference_text:Yoshida H, Onda M, Tajiri T, Uchida E, Arima Y, Mamada Y, Yamamoto K, Kaneko M, Terada Y, Kumazaki T: Experience with intraarterial infusion of styrene maleic acid neocarzinostatin (SMANCS)-lipiodol in pancreatic cancer. Hepatogastroenterology. 1999 Jul-Aug;46(28):2612-5.
pubmed_id:10522050
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