PROPYLENE GLYCOL

Relevant Data

Food Additives Approved in the United States

Flavouring Substances Approved by European Union:

  • Furfuryl acetate [show]

Food Additives Approved by European Union:

General Information

Synonyms: 1,2-DIHYDROXYPROPANE, METHYL GLYCOL, PROPANEDIOL
Chemical Names: 1,2-PROPANEDIOL
CAS number: 57-55-6
COE number: 2065
JECFA number: 925
FEMA number: 2940
INS:

1520
Functional Class: Food Additives
CARRIER_SOLVENT
HUMECTANT
GLAZING_AGENT

From apps.who.int

Evaluations

Evaluation year: 2002
ADI: 0-25 mg/kg bw (1973)
Meeting: 49
Specs Code: R (1997)
Comments: Evaluation not finalized, pending definition of "flavouring agent"
Report: TRS 913-JECFA 59/112
Tox Monograph: FAS 48-JECFA 57/333 (2001)
Specification: COMPENDIUM ADDENDUM 12/FNP 52 Add. 12/68 (METALS LIMITS) (2004). R; FAO JECFA Monographs 1 vol.3/187

From apps.who.int

GSFA Provisions for PROPYLENE GLYCOL

Number Food Category Max Level Notes
05.1.3

Cocoa-based spreads, including fillings

 1,000 mg/kg Note XS86
06.4.1

Fresh pastas and noodles and like products

 20,000 mg/kg Note 370
04.1.2.8

Fruit preparations, including pulp, purees, fruit toppings and coconut milk

 2,000 mg/kg Note XS240,Note XS314R
06.4.3

Pre-cooked pastas and noodles and like products

 10,000 mg/kg Note 194
05.2.2

Soft candy

 4,500 mg/kg Note XS309R

From www.fao.org

Computed Descriptors

Download SDF
2D Structure
CID1030
IUPAC Namepropane-1,2-diol
InChIInChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3
InChI KeyDNIAPMSPPWPWGF-UHFFFAOYSA-N
Canonical SMILESCC(CO)O
Molecular FormulaC3H8O2
Wikipediapropylene glycol

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight76.095
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Complexity20.9
CACTVS Substructure Key Fingerprint A A A D c c B A M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A C A A A C B S g g A I C A A A A A g A A A A A A A A A A A A A A A A A A A A A A A A A B E A A A A A A A Q A A A A A A B A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area40.5
Monoisotopic Mass76.052
Exact Mass76.052
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count5
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem

Food Additives Biosynthesis/Degradation

ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.7184
Human Intestinal AbsorptionHIA+0.9832
Caco-2 PermeabilityCaco2-0.6594
P-glycoprotein SubstrateNon-substrate0.7162
P-glycoprotein InhibitorNon-inhibitor0.9157
Non-inhibitor0.9440
Renal Organic Cation TransporterNon-inhibitor0.9401
Distribution
Subcellular localizationMitochondria0.5057
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8320
CYP450 2D6 SubstrateNon-substrate0.8739
CYP450 3A4 SubstrateNon-substrate0.7434
CYP450 1A2 InhibitorNon-inhibitor0.7858
CYP450 2C9 InhibitorNon-inhibitor0.9388
CYP450 2D6 InhibitorNon-inhibitor0.9526
CYP450 2C19 InhibitorNon-inhibitor0.8969
CYP450 3A4 InhibitorNon-inhibitor0.9599
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9580
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9568
Non-inhibitor0.9008
AMES ToxicityNon AMES toxic0.9132
CarcinogensCarcinogens 0.5000
Fish ToxicityLow FHMT0.9032
Tetrahymena Pyriformis ToxicityLow TPT0.9973
Honey Bee ToxicityHigh HBT0.6370
BiodegradationReady biodegradable0.9505
Acute Oral ToxicityIV0.6282
Carcinogenicity (Three-class)Non-required0.7445

From admetSAR

ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility1.3774LogS
Caco-2 Permeability0.5065LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity0.6112LD50, mol/kg
Fish Toxicity3.6991pLC50, mg/L
Tetrahymena Pyriformis Toxicity-2.7956pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of ExposureNone
Mechanism of ToxicityNone
MetabolismNone
Toxicity ValuesNone
Lethal DoseNone
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNone
Health EffectsNone
TreatmentNone
Reference
  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. Zar T, Graeber C, Perazella MA: Recognition, treatment, and prevention of propylene glycol toxicity. Semin Dial. 2007 May-Jun;20(3):217-9.[17555487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. Reichard GA Jr, Skutches CL, Hoeldtke RD, Owen OE: Acetone metabolism in humans during diabetic ketoacidosis. Diabetes. 1986 Jun;35(6):668-74.[3086164 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]

From T3DB

Taxonomic Classification

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassAlcohols and polyols
Intermediate Tree NodesPolyols
Direct Parent1,2-diols
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsSecondary alcohol - 1,2-diol - Hydrocarbon derivative - Primary alcohol - Aliphatic acyclic compound
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.

From ClassyFire

Targets

Target Details

Coagulation factor XIII A chain

General Function:
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:
83266.805 Da
References
  1. 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 ]
Target Details

Bile acid receptor

General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
Gene Name:
NR1H4
Uniprot ID:
Q96RI1
Molecular Weight:
55913.915 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details

Haloalkane dehalogenase

General Function:
Haloalkane dehalogenase activity
Specific Function:
Catalyzes hydrolytic cleavage of carbon-halogen bonds in halogenated aliphatic compounds, leading to the formation of the corresponding primary alcohols, halide ions and protons. Has a broad substrate specificity since not only monochloroalkanes (C3 to C10) but also dichloroalkanes (> C3), bromoalkanes, and chlorinated aliphatic alcohols were good substrates. Shows almost no activity with 1,2-dichloroethane, but very high activity with the brominated analog. Is involved in the degradation of the important environmental pollutant gamma-hexachlorocyclohexane (lindane) as it also catalyzes conversion of 1,3,4,6-tetrachloro-1,4-cyclohexadiene (1,4-TCDN) to 2,5-dichloro-2,5-cyclohexadiene-1,4-diol (2,5-DDOL) via the intermediate 2,4,5-trichloro-2,5-cyclohexadiene-1-ol (2,4,5-DNOL).
Gene Name:
linB
Uniprot ID:
P51698
Molecular Weight:
33107.275 Da
Target Details

Clavaminate synthase 1

General Function:
Iron ion binding
Gene Name:
cs1
Uniprot ID:
Q05581
Molecular Weight:
35369.325 Da
Target Details

Lactaldehyde reductase

General Function:
Lactaldehyde reductase activity
Gene Name:
fucO
Uniprot ID:
P0A9S1
Molecular Weight:
40513.025 Da
Target Details

B12-independent glycerol dehydratase

General Function:
Catalytic activity
Gene Name:
dhaB1
Uniprot ID:
Q8GEZ8
Molecular Weight:
88046.08 Da

From T3DB