Monobutyl phthalate

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Monobutyl phthalate
Monobutylphthalate Structural Formula.svg
Names
Preferred IUPAC name
2-(Butoxycarbonyl)benzoic acid
Other names
1,2-Benzenedicarboxylic acid, monobutyl ester[1]
2-(Butoxycarbonyl)benzoic acid[1]
Butyl hydrogenphthalate[1]
Mono-n-butyl phthalate[1]
Phthalic acid, monobutyl ester[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.580 Edit this at Wikidata
EC Number
  • 205-036-2
UNII
  • InChI=1S/C12H14O4/c1-2-3-8-16-12(15)10-7-5-4-6-9(10)11(13)14/h4-7H,2-3,8H2,1H3,(H,13,14)
    Key: YZBOVSFWWNVKRJ-UHFFFAOYSA-N
  • CCCCOC(=O)C1=CC=CC=C1C(=O)O
Properties
C12H14O4
Molar mass 222.240 g·mol−1
Appearance White solid
Melting point 73.5 °C (164.3 °F; 346.6 K)
Hazards
GHS labelling:
GHS08: Health hazard
Danger
H360
P201, P202, P281, P308+P313, P405, P501
Lethal dose or concentration (LD, LC):
1,000 mg kg−1 (mouse, intraperitoneal)[1][2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Monobutyl phthalate (MBP) is an organic compound with the condensed structural formula CH3(CH2)3OOCC6H4COOH. It is a white solid that features both an butyl ester group and a carboxylic acid group. It is the major metabolite of dibutyl phthalate. Like many phthalates, MBP has attracted attention as a potential endocrine disruptor.[3]

MBP is also the secondary metabolite of butyl benzyl phthalate, less than monobenzyl phthalate (MBzP). It hydrolyses to phthalic acid and 1-butanol.[4]

References[edit]

  1. ^ a b c d e f "Monobutyl phthalate". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. January 4, 2020. Retrieved January 10, 2020.
  2. ^ Chambon, Pierre; Riotte, Maurice; Daudon, Marc; Chambon-Mougenot, Renée; Bringuier, Janine (1971). "Etude du métabolisme des phtalates de dibutyle et de diéthyle chez le Rat" [Metabolism of dibutyl and diethyl phthalates in the rat]. Comptes Rendus de l'Académie des Sciences, Série D (in French). 273 (22): 2165–2168. PMID 5003086.
  3. ^ Hu Y, Dong C, Chen M, Chen Y, Gu A, Xia Y, Sun H, Li Z, Wang Y (2015). "Effects of monobutyl phthalate on steroidogenesis through steroidogenic acute regulatory protein regulated by transcription factors in mouse Leydig tumor cells". Journal of Endocrinological Investigation. 38 (8): 875–884. doi:10.1007/s40618-015-0279-6. PMID 25903692. S2CID 21965989.
  4. ^ Huang, Jingyu; Nkrumah, Philip N.; Li, Yi; Appiah-Sefah, Gloria (2013). "Chemical Behavior of Phthalates Under Abiotic Conditions in Landfills". Reviews of Environmental Contamination and Toxicology. Vol. 224. New York, NY: Springer Science+Business Media. pp. 39–52. doi:10.1007/978-1-4614-5882-1_2. ISBN 9781461458814. PMID 23232918.