Monobenzyl phthalate

Monobenzyl phthalate
Names
	Preferred IUPAC name 2-[(Benzyloxy)carbonyl]benzoic acid
	Other names Phthalic Acid Monobenzyl Ester; Benzyl hydrogen phthalate; 1,2-Benzenedicarboxylic acid, mono(phenylmethyl) ester; Mono(phenylmethyl) 1,2-benzenedicarboxylate; 2-phenylmethoxycarbonylbenzoic acid
Identifiers
CAS Number	2528-16-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:132612;
ChEMBL	ChEMBL1466083;
ChemSpider	29430;
ECHA InfoCard	100.017.974
EC Number	219-771-1;
PubChem CID	31736;
UNII	27NM8BNV1K;
CompTox Dashboard (EPA)	DTXSID9043938 ;
	InChI InChI=1S/C15H12O4/c16-14(17)12-8-4-5-9-13(12)15(18)19-10-11-6-2-1-3-7-11/h1-9H,10H2,(H,16,17) Key: XIKIUQUXDNHBFR-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)COC(=O)C2=CC=CC=C2C(=O)O;
Properties
Chemical formula	C15H12O4
Molar mass	256.257 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P264, P280, P305 P351 P338, P337 P313
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Monobenzyl phthalate (MBzP) also known as 1,2-Benzenedicarboxylic acid, 1-(phenylmethyl) ester is an organic compound with the condensed structural formula C₆H₅CH₂OOCC₆H₄COOH. It is the major metabolite of butyl benzyl phthalate(BBP), a common plasticizer.^[2] BBP can also be metabolized into monobutyl phthalate (MBP).^[3]^[4] Like many phthalates, BBP has attracted attention as a potential endocrine disruptor.^[5]^[6]^[7]

References

^ ^a ^b ^c ^d ^e "Monobenzyl phthalate". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. February 29, 2020. Retrieved March 5, 2020.
^ Chatterjee, Subhankar; Karlovsky, Petr (June 2010). "Removal of the endocrine disrupter butyl benzyl phthalate from the environment". Applied Microbiology and Biotechnology. 87 (1): 61–73. doi:10.1007/s00253-010-2570-y. PMC 2872021. PMID 20396882.
^ 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.
^ Saillenfait AM, Sabaté JP, Gallissot F (2002). "Comparative embryotoxicities of butyl benzyl phthalate, mono-n-butyl phthalate and mono-benzyl phthalate in mice and rats: in vivo and in vitro observations". Reproductive Toxicology. 17 (5): 575–83. doi:10.1016/s0890-6238(03)00102-3. PMID 14555196.
^ Du, Zuo; Cao, Yun-Feng; Li, Sai-Nan; Hu, Cui-Min; Fu, Zhi-Wei; Huang, Chun-Ting; Sun, Xiao-Yu; Liu, Yong-Zhe; Yang, Kun; Fang, Zhong-Ze (April 2018). "Inhibition of UDP-glucuronosyltransferases (UGTs) by phthalate monoesters". Chemosphere. 197: 7–13. Bibcode:2018Chmsp.197....7D. doi:10.1016/j.chemosphere.2018.01.010. PMID 29328989.
^ Ema M, Harazono A, Miyawaki E, Ogawa Y (July 1996). "Developmental toxicity of mono-n-benzyl phthalate, one of the major metabolites of the plasticizer n-butyl benzyl phthalate, in rats". Toxicology Letters. 86 (1): 19–25. doi:10.1016/0378-4274(96)03665-x. PMID 8685916.
^ Ema M, Harazono A, Miyawaki E, Ogawa Y (1995). "Characterization of developmental toxicity of mono-n-benzyl phthalate in rats". Reproductive Toxicology. 10 (5): 365–72. doi:10.1016/0890-6238(96)00082-2. PMID 8888408.

[PubChem-1] "Monobenzyl phthalate". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. February 29, 2020. Retrieved March 5, 2020.

[2] Chatterjee, Subhankar; Karlovsky, Petr (June 2010). "Removal of the endocrine disrupter butyl benzyl phthalate from the environment". Applied Microbiology and Biotechnology. 87 (1): 61–73. doi:10.1007/s00253-010-2570-y. PMC 2872021. PMID 20396882.

[:22-3] 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.

[4] Saillenfait AM, Sabaté JP, Gallissot F (2002). "Comparative embryotoxicities of butyl benzyl phthalate, mono-n-butyl phthalate and mono-benzyl phthalate in mice and rats: in vivo and in vitro observations". Reproductive Toxicology. 17 (5): 575–83. doi:10.1016/s0890-6238(03)00102-3. PMID 14555196.

[5] Du, Zuo; Cao, Yun-Feng; Li, Sai-Nan; Hu, Cui-Min; Fu, Zhi-Wei; Huang, Chun-Ting; Sun, Xiao-Yu; Liu, Yong-Zhe; Yang, Kun; Fang, Zhong-Ze (April 2018). "Inhibition of UDP-glucuronosyltransferases (UGTs) by phthalate monoesters". Chemosphere. 197: 7–13. Bibcode:2018Chmsp.197....7D. doi:10.1016/j.chemosphere.2018.01.010. PMID 29328989.

[6] Ema M, Harazono A, Miyawaki E, Ogawa Y (July 1996). "Developmental toxicity of mono-n-benzyl phthalate, one of the major metabolites of the plasticizer n-butyl benzyl phthalate, in rats". Toxicology Letters. 86 (1): 19–25. doi:10.1016/0378-4274(96)03665-x. PMID 8685916.

[7] Ema M, Harazono A, Miyawaki E, Ogawa Y (1995). "Characterization of developmental toxicity of mono-n-benzyl phthalate in rats". Reproductive Toxicology. 10 (5): 365–72. doi:10.1016/0890-6238(96)00082-2. PMID 8888408.

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