6PPD-quinone
- Product Name
- 6PPD-quinone
- CAS No.
- 2754428-18-5
- Chemical Name
- 6PPD-quinone
- Synonyms
- 6PPD-Q;6PPD-quinone;Phentolamine Impurity 31;N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine quinone;2-[(1,3-dimethylbutyl)amino]-5-(phenylamino)-2,5-cyclohexadiene-1,4-dione;2-((4-methylpentan-2-yl)amino)-5-(phenylamino)cyclohexa-2,5-diene-1,4-dione;2,5-Cyclohexadiene-1,4-dione, 2-[(1,3-dimethylbutyl)amino]-5-(phenylamino)-;2- ((4-methylpent-2-yl) amino) -5- (phenylamino) cyclohex-2,5-diene-1,4-dione;(R)-2-((4-methylpentan-2-yl)amino)-5-(phenylamino)cyclohexa-2,5-diene-1,4-dione;(S)-3,6-dimethylene-N1-(4-methylpentan-2-yl)-N4-phenylcyclohexa-1,4-diene-1,4- diamine
- CBNumber
- CB810899610
- Molecular Formula
- C18H22N2O2
- Formula Weight
- 298.38
- MOL File
- 2754428-18-5.mol
6PPD-quinone Property
- Boiling point:
- 442.2±45.0 °C(Predicted)
- Density
- 1.12±0.1 g/cm3(Predicted)
- solubility
- Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- Solid
- pka
- 0.61±0.20(Predicted)
- color
- Dark Orange to Dark Red
- InChI
- InChI=1S/C18H22N2O2/c1-12(2)9-13(3)19-15-10-18(22)16(11-17(15)21)20-14-7-5-4-6-8-14/h4-8,10-13,19-20H,9H2,1-3H3
- InChIKey
- UBMGKRIXKUIXFQ-UHFFFAOYSA-N
- SMILES
- C1(=O)C=C(NC2=CC=CC=C2)C(=O)C=C1NC(C)CC(C)C
6PPD-quinone Chemical Properties,Usage,Production
Description
6PPD-quinone is an oxidized derivative of the tire antiozonant and substituted p-phenylenediamine 6-PPD. It is toxic to rainbow trout (O. mykiss) and brook trout (S. fontinalis; LC50s = 0.59 and 1.96 μg/L, respectively) but not to arctic char (S. alpinus) and white sturgeon (A. transmontanus; LC50s = >12.7 μg/L for both). 6PPD-quinone (10 μg/L) induces cell death and germline DNA damage and decreases the number of mitotic cells in C. elegans gonads. Urine levels of 6-PPD-quinone are increased in pregnant women compared to non-pregnant adults and children.
Biochem/physiol Actions
Studies have shown that 6PPD/6PPD-quinone can interact with human serum albumin (HSA). It spontaneously inserts into the I-site of HSA, forming a binary complex that induces changes in the secondary structure of HSA. However, their effects on the esterase-like activity of HSA are polarised. 6PPD activates the esterase-like activity of HSA, whereas 6PPD-quinone inhibits it. Molecular docking analyses showed that 6PPD and 6PPD-quinone interact with many amino acid residues on HSA, including TRP214, ARG222, ARG218, ALA291, and PHE211. π-electrons on the benzene ring of 6PPD/6PPD-quinone play a key role in maintaining the stability of the complex. In addition, the stronger binding affinity between 6PPD and HSA compared to 6PPD-quinone could be attributed to the greater negative surface potential of 6PPD.
Safety
6PPD-quinone (6PPD-q) is an oxidation product of the antioxidant N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD) present in rubber. Studies have shown that 6PPD and 6PPD- q are also present in human urine, including adults, children, and pregnant women, and that urinary 6PPD- q concentrations were significantly higher than 6PPD; pregnant women had significantly higher concentrations of 6PPD and 6PPD- q (median 0.068 and 2.91 ng/mL, respectively) than adults (0.018 and 0.40 ng/mL) and children (0.015 and 0.076 ng/mL). The high daily urinary excretion of 6PPD-Q in pregnant women was estimated to be 273 (ng/kg bw)/day. 6PPD-Q is a lethal toxicant to a wide range of aquatic species, and its potential risk to human health from long-term exposure requires urgent attention.
6PPD-quinone Preparation Products And Raw materials
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