Glycidol
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Basic Info
| Common Name | Glycidol(F05291) |
| 2D Structure | |
| Description | Glycidol is an organic compound that contains both epoxide and alcohol functional groups. Being bifunctional, it has a variety of industrial uses. The compound is a slightly viscous liquid that is slightly unstable and is not often encountered in pure form. Glycidol is an irritant of the skin, eyes, mucous membranes, and upper respiratory tract. Exposure to glycidol may also cause central nervous system depression, followed by central nervous system stimulation. |
| FRCD ID | F05291 |
| CAS Number | 556-52-5 |
| PubChem CID | 11164 |
| Formula | C3H6O2 |
| IUPAC Name | oxiran-2-ylmethanol |
| InChI Key | CTKINSOISVBQLD-UHFFFAOYSA-N |
| InChI | InChI=1S/C3H6O2/c4-1-3-2-5-3/h3-4H,1-2H2 |
| Canonical SMILES | C1C(O1)CO |
| Isomeric SMILES | C1C(O1)CO |
| Wikipedia | Glycidol |
| Synonyms |
Oxiranylmethanol
GLYCIDOL
556-52-5
oxiran-2-ylmethanol
Oxiranemethanol
2,3-Epoxy-1-propanol
Epihydrin alcohol
1-Propanol, 2,3-epoxy-
Glycide
3-Hydroxypropylene oxide
|
| Classifies |
Predicted: Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Epoxides |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Epoxides |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | Oxacycle - Ether - Oxirane - Dialkyl ether - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as epoxides. These are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms). |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 74.079 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 1 |
| Complexity | 35.9 |
| Monoisotopic Mass | 74.037 |
| Exact Mass | 74.037 |
| XLogP | -0.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 5 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9702 |
| Human Intestinal Absorption | HIA+ | 0.9581 |
| Caco-2 Permeability | Caco2- | 0.5751 |
| P-glycoprotein Substrate | Non-substrate | 0.7256 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9158 |
| Non-inhibitor | 0.9046 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8342 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6079 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8479 |
| CYP450 2D6 Substrate | Non-substrate | 0.8504 |
| CYP450 3A4 Substrate | Non-substrate | 0.7718 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7861 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7997 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9290 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6898 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9735 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9000 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9383 |
| Non-inhibitor | 0.9332 | |
| AMES Toxicity | AMES toxic | 0.9662 |
| Carcinogens | Non-carcinogens | 0.7233 |
| Fish Toxicity | Low FHMT | 0.9874 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.8456 |
| Honey Bee Toxicity | High HBT | 0.7094 |
| Biodegradation | Ready biodegradable | 0.7561 |
| Acute Oral Toxicity | II | 0.7160 |
| Carcinogenicity (Three-class) | Danger | 0.7487 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.1990 | LogS |
| Caco-2 Permeability | 1.3851 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2771 | LD50, mol/kg |
| Fish Toxicity | 3.0690 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.2684 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Estimated US infant exposures to 3-MCPD esters and glycidyl esters fromconsumption of infant formula. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018Jun | 29620437 |
| Occurrence of 3-monochloropropanediol esters and glycidyl esters in commercialinfant formulas in the United States. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2017Mar | 28004609 |
| [Heat-induced contaminants in foodstuffs : Acrylamide, furan, and fatty acidesters of monochloropropanediols and glycidol]. | Bundesgesundheitsblatt Gesundheitsforschung Gesundheitsschutz | 2017Jul | 28523455 |
| DNA methylation analysis in rat kidney epithelial cells exposed to 3-MCPD andglycidol. | Drug Chem Toxicol | 2017 Oct | 27884059 |
| Measurement of micronuclei and internal dose in mice demonstrates that3-monochloropropane-1,2-diol (3-MCPD) has no genotoxic potency in vivo. | Food Chem Toxicol | 2017 Nov | 28917435 |
| Effects of Triton X-100 and PEG on the Catalytic Properties and Thermal Stabilityof Lipase from Candida Rugosa Free and Immobilized on Glyoxyl-Agarose. | Open Biochem J | 2017 Jul 31 | 29290831 |
| [Biomarkers of internal exposure to toxicologically relevant contaminants in food]. | Bundesgesundheitsblatt Gesundheitsforschung Gesundheitsschutz | 2017 Jul | 28516258 |
| Effects of 3-monochloropropane-1,2-diol (3-MCPD) and its metabolites on DNAdamage and repair under in vitro conditions. | Food Chem Toxicol | 2016 Mar | 26747977 |
| Determination of 3-Monochloropropane-1,2-diol and 2-Monochloropropane-1,3-diol(MCPD) Esters and Glycidyl Esters by Microwave Extraction in DifferentFoodstuffs. | J Agric Food Chem | 2016 Jun 1 | 27133957 |
| Extraction and Liquid Chromatography-Tandem Mass Spectrometry Detection of3-Monochloropropanediol Esters and Glycidyl Esters in Infant Formula. | J Agric Food Chem | 2016 Dec 14 | 27960288 |
| Covalent attachment of lipases on glyoxyl-agarose beads: application in fruitflavor and biodiesel synthesis. | Int J Biol Macromol | 2014 Sep | 24979527 |
| Development of an analytical method for the simultaneous analysis of MCPD esters and glycidyl esters in oil-based foodstuffs. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2014 | 24645641 |
| Toxicology, occurrence and risk characterisation of the chloropropanols in food: 2-monochloro-1,3-propanediol, 1,3-dichloro-2-propanol and 2,3-dichloro-1-propanol. | Food Chem Toxicol | 2013 Aug | 23712097 |
| Occurrence of 3-MCPD and glycidyl esters in edible oils in the United States. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2013 | 24138540 |
| Fatty acid esters of monochloropropanediol (MCPD) and glycidol in refined edible oils. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2013 | 23020600 |
| Simultaneous determination and differentiation of glycidyl esters and3-monochloropropane-1,2-diol (MCPD) esters in different foodstuffs by GC-MS. | J Agric Food Chem | 2011 Jun 8 | 21545150 |
| Toxicological assessment of 3-chloropropane-1,2-diol and glycidol fatty acidesters in food. | Mol Nutr Food Res | 2011 Apr | 21351250 |
| Evaluation of the genotoxic potential of 3-monochloropropane-1,2-diol (3-MCPD)and its metabolites, glycidol and beta-chlorolactic acid, using the single cellgel/comet assay. | Food Chem Toxicol | 2007 Jan | 16971032 |
Targets
- General Function:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- 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 ]