Monobutyl phthalate

Last updated
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-036-2
PubChem CID
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
AppearanceWhite solid
Melting point 73.5 °C (164.3 °F; 346.6 K)
Hazards
GHS classification and labelling:
GHS-pictogram-silhouette.svg
Danger
H360
P201, P202, P281, P308+P313, P405, P501
Lethal dose or concentration (LD, LC):
1,000 mg kg1 (mouse, intraperitoneal) [1] [2]
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]

Related Research Articles

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Thiol Any organic compound having a sulfanyl group

A thiol or thiol derivative is any organosulfur compound of the form R−SH, where R represents an alkyl or other organic substituent. The –SH functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols, and the word is a blend of "thio-" with "alcohol", where the first word deriving from Greek θεῖον (theion) meaning "sulfur".

Butyric acid carboxylic acid with chemical formula CH3CH2CH2CO2H

Butyric acid (from Ancient Greek: βούτῡρον, meaning "butter"), also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H. It is an oily, colorless liquid with an unpleasant odor. Isobutyric acid (2-methylpropanoic acid) is an isomer. Salts and esters of butyric acid are known as butyrates or butanoates. The acid does not occur widely in nature, but its esters are widespread. It is a common industrial chemical and an important component in the mammalian gut.

Phthalate Any ester derived from phthalic acid

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Safrole Chemical compound

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Myelin basic protein

Myelin basic protein (MBP) is a protein believed to be important in the process of myelination of nerves in the nervous system. The myelin sheath is a multi-layered membrane, unique to the nervous system, that functions as an insulator to greatly increase the velocity of axonal impulse conduction. MBP maintains the correct structure of myelin, interacting with the lipids in the myelin membrane.

Benzyl butyl phthalate Chemical compound

Benzyl butyl phthalate (BBP) is a phthalate, an ester of phthalic acid, benzyl alcohol, and n-butanol. BBP is a clear liquid with the chemical formula C19H20O4. It was mostly used as a plasticizer for PVC. It is considered a toxicant.

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2-Ethylhexanol Chemical compound

2-Ethylhexanol is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a massive scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers. It is encountered in plants, fruits, and wines. The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.

Diisobutyl phthalate Chemical compound

Diisobutyl phthalate (DIBP) is prepared by esterification process of isobutanol and phthalic anhydride. Its structural formula is C6H4(COOCH2CH(CH3)2)2.

1-Butanol Chemical compound

Butan-1-ol, also known as n-butanol is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of butan-1-ol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

Dibutyl phthalate Chemical compound

Dibutyl phthalate (DBP) is an organic compound which is commonly used as a plasticizer because of its low toxicity and wide liquid range. With the chemical formula C6H4(CO2C4H9)2, it is a colorless oil, although commercial samples are often yellow.

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Retinoic acid receptor gamma

Retinoic acid receptor gamma (RAR-γ), also known as NR1B3 is a nuclear receptor encoded by the RARG gene. Adapalene selectively targets retinoic acid receptor beta and retinoic acid receptor gamma and its agonism of the gamma subtype is largely responsible for adapalene's observed effects.

GNMT

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Protocatechuic acid Chemical compound

Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies.

Diethyl phthalate Chemical compound

Diethyl phthalate (DEP) is a phthalate ester, appears as a clear colorless liquid without significant odor. It is more dense than water and insoluble in water; hence, it sinks in water.

Monobenzyl phthalate Chemical compound

Monobenzyl phthalate (MBzP) also known as benzene-1, 2-dicarboxylic acid is an organic compound with the condensed structural formula C6H5CH2OOCC6H4COOH. It is the major metabolite of butyl benzyl phthalate, more than monobutyl phthalate (MBP). Like many phthalates, MBP has attracted attention as a potential endocrine disruptor.

References

  1. 1 2 3 4 5 6 "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. 224. New York, NY: Springer Science+Business Media. pp. 39–52. doi:10.1007/978-1-4614-5882-1_2. ISBN   9781461458814. PMID   23232918.