Showing Compound Card for Propylene glycol (CDB000666)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:49:59 UTC
Updated at2020-12-07 19:07:39 UTC
CannabisDB IDCDB000666
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePropylene glycol
DescriptionPropylene glycol, also known as 1,2-propanediol, belongs to the class of organic compounds known as 1,2-diols. These are polyols containing two adjacent hydroxy groups. Propylene glycol 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 to be used on humans. 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 ). Propylene glycol is also widely used as a solvent for the carrier liquid for e-cigarettes. Propylene glycol occurs naturally, most likely as a catabolic product of sugars by gut microbiota. It has also been detected in the volatile fraction of Cannabis sativa samples (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(R)-1,2-PropanediolChEBI
R-1,2-PROPANEDIOLChEBI
(R)-Propylene glycolChEBI, KEGG
(-)-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
Propylene glycolHMDB
R-(-)-1,2-PropanediolHMDB
R-(-)-Propylene glycolHMDB
alpha-Propylene glycolHMDB
α-Propylene glycolHMDB
Chemical FormulaC3H8O2
Average Molecular Weight76.09
Monoisotopic Molecular Weight76.0524
IUPAC Name(2R)-propane-1,2-diol
Traditional NameR-1,2-propanediol
CAS Registry Number4254-14-2
SMILES
C[C@@H](O)CO
InChI Identifier
InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m1/s1
InChI KeyDNIAPMSPPWPWGF-GSVOUGTGSA-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.
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-60 °CNot Available
Boiling Point188.2 °CWikipedia
Water Solubility1000 mg/mL at 20 °CNot Available
logP-0.92HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-cbc512db1a4c5510015e2020-03-26View Spectrum
GC-MSPropylene glycol, non-derivatized, GC-MS Spectrumsplash10-014j-0900000000-d90655d5a614c4ddf998Spectrum
GC-MSPropylene glycol, 2 TMS, GC-MS Spectrumsplash10-014i-1900000000-ab4a1ff05d1275711170Spectrum
GC-MSPropylene glycol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-a18bede40461dace657bSpectrum
GC-MSPropylene glycol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-6d2345a66e2cf8d2d379Spectrum
GC-MSPropylene glycol, non-derivatized, GC-MS Spectrumsplash10-014j-0900000000-d90655d5a614c4ddf998Spectrum
GC-MSPropylene glycol, non-derivatized, GC-MS Spectrumsplash10-014i-1900000000-ab4a1ff05d1275711170Spectrum
Predicted GC-MSPropylene glycol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a7i-9000000000-6c96c59f8ba2e0e5353e2020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-005d-9000000000-ae07e4049d24341335ec2020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00aj-9000000000-f455f8f0f79f9970711a2020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0002-9000000000-c5bf57086deb14e124952020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0002-9000000000-6d2345a66e2cf8d2d3792020-03-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-0a1a58ae50ca7bfbc92f2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-4f58eaf424aa13185ca22015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-d0e5def95a7a7879dc712015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-5bf5d9d3c7cf604af9a32015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9000000000-ea5b27ac0cc585591f632015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-ecc48f7be3304c6cc1e02015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-9000000000-ea4d9d80ebf7615e68112021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-a77309b9b0e17e94870d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-7bb23415e61ec73a459c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-9000000000-5dba4634f494296e13472021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-2174cc6a153316ad8c522021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a1a685f935041163641b2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 500 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Aldose reductaseAKR1B17q35P15121 details
Aldo-keto reductase family 1 member B10AKR1B10O60218 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Coagulation factor XIII A chainF13A16p25.3-p24.3P00488 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
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
References
General References
  1. Zar T, Graeber C, Perazella MA: Recognition, treatment, and prevention of propylene glycol toxicity. Semin Dial. 2007 May-Jun;20(3):217-9. doi: 10.1111/j.1525-139X.2007.00280.x. [PubMed:17555487 ]
  2. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Enzymes

Enzyme Details
1. Aldose reductase
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
Enzyme Details
2. Aldo-keto reductase family 1 member B10
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