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Record Information
Version1.0
Created at2006-02-24 13:28:50 UTC
Updated at2022-04-04 17:16:52 UTC
NP-MRD IDNP0000101
Secondary Accession NumbersNone
Natural Product Identification
Common NamePropylene glycol
DescriptionPropylene glycol (CAS: 57-55-6), Also known as 1,2-propanediol, is an organic compound (a diol alcohol), usually a tasteless, odourless, and colourless 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 the 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 the 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
(R)-1,2-PropanediolChEBI
(R)-Propylene glycolChEBI
R-1,2-PROPANEDIOLChEBI
(-)-1,2-PropanediolHMDB
(-)-Propylene glycolHMDB
(2R)-1,2-PropanediolHMDB
(2R)-Propane-1,2-diolHMDB
(R)-(-)-1,2-PropanediolHMDB
(R)-2-Hydroxy-1-propanolHMDB
1,2-(RS)-PropanediolHMDB
1,2-DihydroxypropaneHMDB
1,2-PropanediolHMDB
1,2-Propylene glycolHMDB
1-Deoxy-sn-glycerolHMDB
2,3-PropanediolHMDB
2-HydroxypropanolHMDB
D-(-)-PropanediolHMDB
Isopropylene glycolHMDB
Methylethyl glycolHMDB
Methylethylene glycolHMDB
Monopropylene glycolHMDB
R-(-)-1,2-PropanediolHMDB
R-(-)-Propylene glycolHMDB
alpha-Propylene glycolHMDB
Α-propylene glycolHMDB
Propylene glycolHMDB
Chemical FormulaC3H8O2
Average Mass76.0944 Da
Monoisotopic Mass76.05243 Da
IUPAC Name(2R)-propane-1,2-diol
Traditional NameR-1,2-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 KeyDNIAPMSPPWPWGF-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-04-04View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-04-04View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agaricus bisporusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Arabidopsis thalianaPlant
Cannabis sativaCannabisDB
      Not Available
Escherichia coliBacteria
Homo sapiens (Serum)Animalia
Homo sapiens (Urine)Animalia
Pleurotus ostreatusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
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
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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility952 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity18.97 m³·mol⁻¹ChemAxon
Polarizability8.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001881
DrugBank IDDB02159
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008274
KNApSAcK IDC00007410
Chemspider ID228188
KEGG Compound IDC02912
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropylene_glycol
METLIN IDNot Available
PubChem Compound259994
PDB IDNot Available
ChEBI ID28972
Good Scents IDNot Available
References
General References
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  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. [PubMed: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. [PubMed:14535099 ]
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  8. Reichard GA Jr, Skutches CL, Hoeldtke RD, Owen OE: Acetone metabolism in humans during diabetic ketoacidosis. Diabetes. 1986 Jun;35(6):668-74. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:17555487 ]
  20. Kulo A, Smits A, Naulaers G, de Hoon J, Allegaert K: Biochemical tolerance during low dose propylene glycol exposure in neonates: A formulation-controlled evaluation. Daru. 2012;20(1):5. doi: 10.1186/1560-8115-20-5. Epub 2012 Jul 19. [PubMed:23230503 ]