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Record Information
Version3.6
Creation Date2006-02-24 13:28:50 UTC
Update Date2016-08-17 21:43:24 UTC
HMDB IDHMDB01881
Secondary Accession NumbersNone
Metabolite Identification
Common NamePropylene glycol
DescriptionPropylene 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 human 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
Thumb
Synonyms
ValueSource
1,2-PropanediolKegg
(RS)-1,2-PropanediolHMDB
1,2-(RS)-PropanediolHMDB
1,2-DihydroxypropaneHMDB
1,2-Propylene glycolHMDB
1,2-PropylenglykolHMDB
2,3-PropanediolHMDB
2-HydroxypropanolHMDB
a-Propylene glycolHMDB
Aliphatic alcoholHMDB
alpha-Propylene glycolHMDB
Chilisa feHMDB
DL-1,2-PropanediolHMDB
DL-Propylene glycolHMDB
DowfrostHMDB
GlycolHMDB
Ilexan PHMDB
Inhibited 1,2-propylene glycolHMDB
Isopropylene glycolHMDB
Methyl glycolHMDB
Methylethyl glycolHMDB
Methylethylene glycolHMDB
Monopropylene glycolHMDB
ProlugenHMDB
Propane-1,2-diolHMDB
PropanediolHMDB
Propylene glycol uspHMDB
PropylenglycolHMDB
Sentry propylene glycolHMDB
SirleneHMDB
Solar winter banHMDB
Solargard PHMDB
Trimethyl glycolHMDB
Ucar 35HMDB
Chemical FormulaC3H8O2
Average Molecular Weight76.0944
Monoisotopic Molecular Weight76.0524295
IUPAC Namepropane-1,2-diol
Traditional Name1,2-propanediol
CAS Registry Number57-55-6
SMILES
CC(O)CO
InChI Identifier
InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3
InChI KeyInChIKey=DNIAPMSPPWPWGF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassAlcohols and polyols
Sub ClassPolyols
Direct Parent1,2-diols
Alternative Parents
Substituents
  • Secondary alcohol
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Cosmetic
  • Drug
  • Food
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-60 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogP-0.92HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility952.0 mg/mLALOGPS
logP-1.1ALOGPS
logP-0.79ChemAxon
logS1.1ALOGPS
pKa (Strongest Acidic)14.47ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity18.97 m3·mol-1ChemAxon
Polarizability8.01 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014j-0900000000-d90655d5a614c4ddf998View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-1900000000-ab4a1ff05d1275711170View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a7i-9000000000-6c96c59f8ba2e0e5353eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-005d-9000000000-ae07e4049d24341335ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00aj-9000000000-f455f8f0f79f9970711aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0002-9000000000-c5bf57086deb14e12495View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0002-9000000000-6d2345a66e2cf8d2d379View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-cbc512db1a4c5510015eView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Intestine
  • Muscle
  • Nerve Cells
  • Platelet
  • Skin
  • Stratum Corneum
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Leigh SyndromeSMP00196Not Available
Primary hyperoxaluria II, PH2SMP00558Not Available
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)SMP00334Not Available
Pyruvate Dehydrogenase Complex DeficiencySMP00212Not Available
Pyruvate kinase deficiencySMP00559Not Available
Pyruvate MetabolismSMP00060map00620
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified22.3 +/- 3.3 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.0 (0.0-5.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified33 +/- 50 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.63 +/- 0.4 (0 - 1.0) uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Not AvailableNormal details
SalivaDetected and Quantified3 (<1-50) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified20 (<1-178) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified17 (<1-84) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified8 (<1-46) uMAdult (>18 years old)Female
Normal
details
SalivaDetected and Quantified1-121 uMAdult (>18 years old)Male
normal
details
SalivaDetected and Quantified1-140 uMAdult (>18 years old)Male
normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified26.76 +/- 21.09 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified>10 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified20.586 +/- 22.556 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified6.7 (1.4-44.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified36.3 +/- 19.9 uMAdult (>18 years old)BothHeart Transplant details
BloodDetected and Quantified15.0 (5.0-35.4) uMAdult (>18 years old)Both
Cirrhosis
details
UrineDetected and Quantified2.0 (0.0-31.0) umol/mmol creatinineNot SpecifiedBothLung cancer details
UrineDetected and Quantified150.63 +/- 491.323 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Cirrhosis
  1. Casazza JP, Frietas J, Stambuk D, Morgan MY, Veech RL: The measurement of 1,2-propanediol, D, L-2,3-butanediol and meso-2,3-butanediol in controls and alcoholic cirrhotics. Alcohol Alcohol Suppl. 1987;1:607-9. [3426740 ]
Lung Cancer
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. [18953024 ]
Associated OMIM IDs
DrugBank IDDB01839
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008274
KNApSAcK IDC00007410
Chemspider ID13835224
KEGG Compound IDC00583
BioCyc IDPROPANE-1,2-DIOL
BiGG IDNot Available
Wikipedia Link1,2-Propanediol
NuGOwiki LinkHMDB01881
Metagene LinkHMDB01881
METLIN ID3220
PubChem Compound1030
PDB IDNot Available
ChEBI ID16997
References
Synthesis ReferenceTuck, Michael William Marshall. Preparation of propylene glycol by hydrogenation of glycerol. PCT Int. Appl. (2008), 20pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [12097436 ]
  2. Brucks R, Nanavaty M, Jung D, Siegel F: The effect of ultrasound on the in vitro penetration of ibuprofen through human epidermis. Pharm Res. 1989 Aug;6(8):697-701. [2813262 ]
  3. Claverie F, Giordano-Labadie F, Bazex J: [Contact eczema induced by propylene glycol. Concentration and vehicle adapted for for patch tests] Ann Dermatol Venereol. 1997;124(4):315-7. [9739936 ]
  4. Li N, Liu Z, Jia X, Cui W, Wang W, Zhang X, Han C, Chen J, Wang M: [Study on the toxicological effect of chloropropanols on rats] Wei Sheng Yan Jiu. 2003 Jul;32(4):349-52. [14535099 ]
  5. Maltaris T, Dimmler A, Muller A, Binder H, Hoffmann I, Kohl J, Siebzehnrubl E, Beckmann MW, Dittrich R: The use of an open-freezing system with self-seeding for cryopreservation of mouse ovarian tissue. Reprod Domest Anim. 2005 Jun;40(3):250-4. [15943700 ]
  6. Li GL, van der Geest R, Chanet L, van Zanten E, Danhof M, Bouwstra JA: In vitro iontophoresis of R-apomorphine across human stratum corneum. Structure-transport relationship of penetration enhancement. J Control Release. 2002 Nov 7;84(1-2):49-57. [12399167 ]
  7. Fare JC, Guesnon P, Helouis JJ, Normand S, Andre JL, Duvaldestin P: [Intramuscular premedication with diazepam in a fat emulsion] Cah Anesthesiol. 1984 May-Jun;32(4):303-6. [6529665 ]
  8. Reichard GA Jr, Skutches CL, Hoeldtke RD, Owen OE: Acetone metabolism in humans during diabetic ketoacidosis. Diabetes. 1986 Jun;35(6):668-74. [3086164 ]
  9. Casazza JP, Frietas J, Stambuk D, Morgan MY, Veech RL: The measurement of 1,2-propanediol, D, L-2,3-butanediol and meso-2,3-butanediol in controls and alcoholic cirrhotics. Alcohol Alcohol Suppl. 1987;1:607-9. [3426740 ]
  10. Vaddi HK, Ho PC, Chan YW, Chan SY: Oxide terpenes as human skin penetration enhancers of haloperidol from ethanol and propylene glycol and their modes of action on stratum corneum. Biol Pharm Bull. 2003 Feb;26(2):220-8. [12576684 ]
  11. Fernandez C, Marti-Mestres G, Ramos J, Maillols H: LC analysis of benzophenone-3: II application to determination of 'in vitro' and 'in vivo' skin penetration from solvents, coarse and submicron emulsions. J Pharm Biomed Anal. 2000 Dec;24(1):155-65. [11108549 ]
  12. Vaddi HK, Ho PC, Chan SY: Terpenes in propylene glycol as skin-penetration enhancers: permeation and partition of haloperidol, Fourier transform infrared spectroscopy, and differential scanning calorimetry. J Pharm Sci. 2002 Jul;91(7):1639-51. [12115825 ]
  13. Gancevici GG: Role of complement inhibition in topical therapy of muco-cutaneous herpes simplex virus infections. Roum Arch Microbiol Immunol. 1993 Oct-Dec;52(4):293-303. [7827366 ]
  14. Liu JH, Gao D, He LQ, Moey LK, Hua K, Liu ZB: The phase diagram for the ternary system propylene glycol-sodium chloride-water and their application to platelet cryopreservation. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2003 Feb;11(1):92-5. [12667299 ]
  15. Rajasenan RS, Riley RJ, Leeder JS: Expression and inducibility of antigens in severe combined immunodeficient mice recognized by human anti-P450 antibodies. Toxicol Appl Pharmacol. 1995 Nov;135(1):89-99. [7482543 ]
  16. Decherchi P, Lammari-Barreault N, Cochard P, Carin M, Rega P, Pio J, Pellissier JF, Ladaique P, Novakovitch G, Gauthier P: CNS axonal regeneration with peripheral nerve grafts cryopreserved by vitrification: cytological and functional aspects. Cryobiology. 1997 May;34(3):214-39. [9160994 ]
  17. Trottet L, Owen H, Holme P, Heylings J, Collin IP, Breen AP, Siyad MN, Nandra RS, Davis AF: Are all aciclovir cream formulations bioequivalent? Int J Pharm. 2005 Nov 4;304(1-2):63-71. Epub 2005 Sep 1. [16139970 ]
  18. Miller DL, Wildnauer RH: Thermoanalytical probes for the analysis of physical properties of stratum corneum. J Invest Dermatol. 1977 Sep;69(3):287-9. [894064 ]
  19. Zar T, Graeber C, Perazella MA: Recognition, treatment, and prevention of propylene glycol toxicity. Semin Dial. 2007 May-Jun;20(3):217-9. [17555487 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular weight:
35853.125
Reactions
Propylene glycol + NADP → Lactaldehyde + NADPH + Hydrogen Iondetails
General function:
Involved in protein-glutamine gamma-glutamyltransferase activity
Specific function:
Factor XIII is activated by thrombin and calcium ion to a transglutaminase that catalyzes the formation of gamma-glutamyl-epsilon-lysine cross-links between fibrin chains, thus stabilizing the fibrin clot. Also cross-link alpha-2-plasmin inhibitor, or fibronectin, to the alpha chains of fibrin.
Gene Name:
F13A1
Uniprot ID:
P00488
Molecular weight:
83267.785
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
General function:
Not Available
Specific function:
Acts as all-trans-retinaldehyde reductase. Can efficiently reduce aliphatic and aromatic aldehydes, and is less active on hexoses (in vitro). May be responsible for detoxification of reactive aldehydes in the digested food before the nutrients are passed on to other organs.
Gene Name:
AKR1B10
Uniprot ID:
O60218
Molecular weight:
Not Available
Reactions
Propylene glycol + NADP → Lactaldehyde + NADPH + Hydrogen Iondetails