Livestock Metabolome Database: Showing metabocard for Propylene glycol (LMDB00360)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:48:06 UTC

Update Date

2020-03-19 21:20:57 UTC

Lmdb

LMDB00360

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Propylene glycol

Description

Propylene glycol (1,2-propanediol) is an organic compound (a diol alcohol), usually a tasteless, odorless, and colorless clear oily liquid that is hygroscopic and miscible with water, acetone, and chloroform. It is manufactured by the hydration of propylene oxide. Propylene glycol is used as a solvent for intravenous, oral, and topical pharmaceutical preparations It is generally considered safe. However in large doses it can be toxic, especially if given over a short period of time. Intravenous lorazepam contains the largest amount of propylene glycol of commonly used drugs. In adults with normal liver and kidney function, the terminal half-life of propylene glycol ranges from 1.4 to 3.3 hours. Propylene glycol is metabolized by the liver to form lactate, acetate, and pyruvate. The nonmetabolized drug is excreted in the urine mainly as the glucuronide conjugate, approximately 12 to 45 percent is excreted unchanged in urine. Renal clearance decreases as the dose administered increases (390 ml/minute/173 m2 at a dose of 5 g/day but only 144 ml/minute/173 m2 at a dose of 21 g/day). These data suggest that renal clearance declines at higher propylene glycol doses because of saturation of proximal tubular secretion of the drug. As an acceptable level of propylene glycol has not been defined, the clinical implication of a propylene glycol level is unclear. The World Health Organization (WHO) recommends a maximum consumption of 25 mg/kg/day (1.8 g/day for a 75 kg male) of propylene glycol when used as a food additive, but this limit does not address its use as a drug solvent. No maximum dose is recommended in the literature for intravenous therapy with propylene glycol. Intoxication occurs at much higher doses than the WHO dose limit and is exclusive to pharmacologic exposure. Propylene glycol toxicity includes development of serum hyperosmolality, lactic acidosis, and kidney failure. It has been suggested that proximal tubular necrosis is the cause of acute kidney injury from propylene glycol. Along these lines, proximal tubular cell injury occurs in cultured animal cells exposed to propylene glycol. Acute tubular necrosis was described with propylene glycol toxicity in a case of concomitant administration of intravenous lorazepam and trimethoprim sulfamethoxazole. Propylene glycol induced intoxication can also mimic sepsis or systemic inflammatory response syndrome (SIRS). Patients suspected of having sepsis with negative cultures should be evaluated for propylene glycol toxicity if they have been exposed to high dose lorazepam or other medications containing this solvent. (PMID: 17555487 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Dihydroxypropane	ChEBI
1,2-Propanediol	ChEBI
1,2-Propylenglykol	ChEBI
2-Hydroxypropanol	ChEBI
alpha-Propyleneglycol	ChEBI
CH3CH(OH)CH2OH	ChEBI
HOCH2CH(OH)CH3	ChEBI
HOCH2CH(OH)Me	ChEBI
Isopropylene glycol	ChEBI
MeCH(OH)CH2OH	ChEBI
Methyl glycol	ChEBI
Methylethyl glycol	ChEBI
Methylethylene glycol	ChEBI
Monopropylene glycol	ChEBI
PPD	ChEBI
a-Propyleneglycol	Generator
Α-propyleneglycol	Generator
(RS)-1,2-Propanediol	HMDB
1,2-(RS)-Propanediol	HMDB
1,2-Propylene glycol	HMDB
2,3-Propanediol	HMDB
a-Propylene glycol	HMDB
Aliphatic alcohol	HMDB
alpha-Propylene glycol	HMDB
Chilisa fe	HMDB
DL-1,2-Propanediol	HMDB
DL-Propylene glycol	HMDB
Dowfrost	HMDB
Glycol	HMDB
Ilexan p	HMDB
Inhibited 1,2-propylene glycol	HMDB
Prolugen	HMDB
Propane-1,2-diol	HMDB
Propanediol	HMDB
Propylene glycol usp	HMDB
Propylenglycol	HMDB
Sentry propylene glycol	HMDB
Sirlene	HMDB
Solar winter ban	HMDB
Solargard p	HMDB
Trimethyl glycol	HMDB
Ucar 35	HMDB
Propan-1,2-diol	HMDB
Monohydrate, propylene glycol	HMDB
Propylene glycol, (R)-isomer	HMDB
Propylene glycol, (S)-isomer	HMDB
1,2 Propanediol	HMDB
Glycol, propylene	HMDB
Propylene glycol, (+-)-isomer	HMDB
Propylene glycol monohydrate	HMDB
Propylene glycol sodium salt	HMDB

Chemical Formula

C₃H₈O₂

Average Molecular Weight

76.0944

Monoisotopic Molecular Weight

76.0524295

IUPAC Name

propane-1,2-diol

Traditional Name

1,2-propanediol

CAS Registry Number

57-55-6

SMILES

CC(O)CO

InChI Identifier

InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3

InChI Key

DNIAPMSPPWPWGF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

1,2-diols

Alternative Parents

Substituents

Secondary alcohol
1,2-diol
Hydrocarbon derivative
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

propane-1,2-diols (CHEBI:16997 )
glycol (CHEBI:16997 )
DL-12-Propanediol (PROPANE-1-2-DIOL )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.1	ALOGPS
logP	-0.79	ChemAxon
logS	1.1	ALOGPS
pKa (Strongest Acidic)	14.47	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	18.97 m³·mol⁻¹	ChemAxon
Polarizability	8.01 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014j-0900000000-d90655d5a614c4ddf998	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-1900000000-ab4a1ff05d1275711170	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9000000000-a18bede40461dace657b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9000000000-6d2345a66e2cf8d2d379	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014j-0900000000-d90655d5a614c4ddf998	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-1900000000-ab4a1ff05d1275711170	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-055g-9000000000-594a84f802409d0a8265	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0kp0-9520000000-ffe4848ba88742d1a4d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a7i-9000000000-6c96c59f8ba2e0e5353e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-005d-9000000000-ae07e4049d24341335ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00aj-9000000000-f455f8f0f79f9970711a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0002-9000000000-c5bf57086deb14e12495	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0002-9000000000-6d2345a66e2cf8d2d379	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-0a1a58ae50ca7bfbc92f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-0c246d88e88be8375dd1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-5e6c0456bbcc20afb607	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-5bf5d9d3c7cf604af9a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-9000000000-3499fb432cd119926640	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-36c6bc6082b188beb665	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-cbc512db1a4c5510015e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected and Quantified	1.17 +/- 0.96 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	22761248	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	23255817	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details

External Links

DrugBank ID

DB01839

HMDB ID

HMDB0001881

FooDB ID

FDB008274

Phenol Explorer ID

Not Available

KNApSAcK ID

C00007410

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

3220

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zar T, Graeber C, Perazella MA: Recognition, treatment, and prevention of propylene glycol toxicity. Semin Dial. 2007 May-Jun;20(3):217-9. [17555487 ]

Showing metabocard for Propylene glycol (LMDB00360)

Structure for LMDB00360 (Propylene glycol)