Monobutyl phthalate

Monobutyl phthalate
Names
	Preferred IUPAC name 2-Butoxycarbonylbenzoic acid
	Other names 1,2-Benzenedicarboxylic acid, monobutyl ester; 2-(Butoxycarbonyl)benzoic acid; Butyl hydrogenphthalate; Mono-n-butyl phthalate; Phthalic acid, monobutyl ester
Identifiers
CAS Number	131-70-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:88522;
ChEMBL	ChEMBL2447930;
ChemSpider	8257;
ECHA InfoCard	100.004.580
EC Number	205-036-2;
PubChem CID	8575;
UNII	ZI46LWZ45G;
CompTox Dashboard (EPA)	DTXSID4040002 ;
	InChI 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;
	SMILES CCCCOC(=O)C1=CC=CC=C1C(=O)O;
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H360
Precautionary statements	P201, P202, P281, P308+P313, P405, P501
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	1,000 mg kg−1 (mouse, intraperitoneal)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

^ ^a ^b ^c ^d ^e ^f ^g "Monobutyl phthalate". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. January 4, 2020. Retrieved January 10, 2020.
^ 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 Hebdomadaires des Séances de l'Académie des Sciences, Série D: Sciences Naturelles (in French). 273 (22): 2165–2168. PMID 5003086.
^ Hu Y, Dong C, Chen M, Chen Y, Gu A, Xia Y, Sun H, Li Z, Wang Y. "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.
^ 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.