ChemicalBook Product Catalog Organic Chemistry Inorganic acid Esters Diethyl phosphate

Diethyl phosphate

Product NameDiethyl phosphate
CAS598-02-7
MFC4H11O4P
MW154.1
EINECS209-912-5
MOL File598-02-7.mol

Chemical Properties

Melting point	6 °C
Boiling point	203 °C
Density	1.29
refractive index	1.4170
Flash point	91 °C
storage temp.	Sealed in dry,2-8°C
solubility	Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka	1.42±0.50(Predicted)
form	Liquid
color	Clear colorless to light yellow-orange
Stability	Moisture Sensitive
InChI	InChI=1S/C4H11O4P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3,(H,5,6)
InChIKey	UCQFCFPECQILOL-UHFFFAOYSA-N
SMILES	P(O)(OCC)(OCC)=O
EPA Substance Registry System	Phosphoric acid, diethyl ester (598-02-7)

Safety Information

Hazard Codes	Xi,T,F
Risk Statements	36/37/38-39/23/24/25-23/24/25-11
Safety Statements	37/39-26-36-45-36/37-16-7
RTECS	TC0665000
TSCA	TSCA listed
HS Code	29199000

MSDS

Provider	Language
ACROS	English

Usage And Synthesis

Chemical Properties

clear colorless to light yellow-orange liquid

Uses

Phosphoric acid diethyl ester is an organophosphate that is usually found in pesticides and is known to induce changes in male hormone profile by decreasing serum testosterone and inhibin B levels. Phosphoric acid diethyl ester is also known to negatively affect the health of women and newborns living in agricultural communities.

Definition

ChEBI: A dialkyl phosphate having ethyl as the alkyl group.

Synthesis Reference(s)

The Journal of Organic Chemistry, 28, p. 2089, 1963 DOI: 10.1021/jo01043a035
Tetrahedron Letters, 29, p. 619, 1988 DOI: 10.1016/S0040-4039(00)80165-3

in vivo

Diethyl phosphate (oral gavage; 0.08-0.8 mg/kg; 24 weeks) can lead to the disturbance of endocrine hormones and related metabolic indexes in rats^[1].
Diethyl phosphate (oral gavage; 0.08-0.13 mg/kg; 20 weeks) affects the intestinal microbiota, serum hormones and pro-inflammatory cytokines^[2].

Animal Model:	Adult male Wistar rats aged 7-8 weeks old (344.4 ± 21.0 g)^[1]
Dosage:	0.08 or 0.8 mg/kg
Administration:	Oral gavage (i.g.); 24 weeks
Result:	Did not affect the body weight of rats and food intake. Significantly decreased serum levels of TC, TG and LDL-C in rats. Resulted in a decrease in sperm concentration, while the sperm abnormality rate increased, did not affect the sperm morphology in rats. Increased the serum levels of FSH and estradiol, while the serum levels of LH and testosterone decreased. Could cause thyroid-related hormone disorders in the serum of rats, causing symptoms of hyperthyroidism in rats, and could also lead to abnormal expression of thyroid hormone-related genes in the rat liver.

Animal Model:	Male Wistar rats aged 7 weeks old^[2]
Dosage:	0.08 or 0.13 mg/kg
Administration:	Oral gavage (i.g.); 20 weeks
Result:	Significantly enriched opportunistic pathogens, including Paraprevotella, Parabacteroides, Alloprevotella, and Helicobacter, leading to a decrease in IL-6. Enriched the butyrate-producing genera, Alloprevotella and Intestinimonas, leading to an increase in estradiol and a resulting decrease in total triglycerides (TGs) and low-density lipoprotein cholesterol (LDL-C) in high dose group. Induced increases in peptide tyrosine-tyrosine (PYY) and ghrelin.

Diethyl phosphate

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