Hexylresorcinol
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Basic Info
| Common Name | Hexylresorcinol(F05557) |
| 2D Structure | |
| Description | Hexylresorcinol is a food additive for prevention of enzymic browning in shrimp and fruits Hexylresorcinol belongs to the family of Resorcinols. These are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydrocyl groups at positions 1 and 3. |
| FRCD ID | F05557 |
| CAS Number | 136-77-6 |
| PubChem CID | 3610 |
| Formula | C12H18O2 |
| IUPAC Name | 4-hexylbenzene-1,3-diol |
| InChI Key | WFJIVOKAWHGMBH-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H18O2/c1-2-3-4-5-6-10-7-8-11(13)9-12(10)14/h7-9,13-14H,2-6H2,1H3 |
| Canonical SMILES | CCCCCCC1=C(C=C(C=C1)O)O |
| Isomeric SMILES | CCCCCCC1=C(C=C(C=C1)O)O |
| Synonyms |
4-Hexylresorcinol
hexylresorcinol
4-hexylbenzene-1,3-diol
136-77-6
Antascarin
Ascaricid
Ascarinol
p-Hexylresorcinol
4-n-Hexylresorcinol
Adrover
|
| Classifies |
Predicted: Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenols |
| Subclass | Benzenediols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Resorcinols |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Resorcinol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as resorcinols. These are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 194.274 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 5 |
| Complexity | 147 |
| Monoisotopic Mass | 194.131 |
| Exact Mass | 194.131 |
| XLogP | 3.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| 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+ | 0.7605 |
| Human Intestinal Absorption | HIA+ | 0.9942 |
| Caco-2 Permeability | Caco2+ | 0.7797 |
| P-glycoprotein Substrate | Substrate | 0.5605 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9663 |
| Non-inhibitor | 0.8000 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8472 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8121 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7607 |
| CYP450 2D6 Substrate | Non-substrate | 0.8035 |
| CYP450 3A4 Substrate | Non-substrate | 0.5670 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7135 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.5868 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.7591 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5738 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.6172 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6700 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.6571 |
| Non-inhibitor | 0.6661 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.8438 |
| Fish Toxicity | High FHMT | 0.9488 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9976 |
| Honey Bee Toxicity | High HBT | 0.6490 |
| Biodegradation | Not ready biodegradable | 0.6471 |
| Acute Oral Toxicity | III | 0.7950 |
| Carcinogenicity (Three-class) | Non-required | 0.6938 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.5275 | LogS |
| Caco-2 Permeability | 1.4195 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2991 | LD50, mol/kg |
| Fish Toxicity | 0.0438 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.9253 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Development and validation of an analytical method for the determination of4-hexylresorcinol in food. | Food Chem | 2016 Jan 1 | 26213080 |
| Identification of xenoestrogens in food additives by an integrated in silico and in vitro approach. | Chem Res Toxicol | 2009 Jan | 19063592 |
| Effect of pyrophosphate and 4-hexylresorcinol pretreatment on quality ofrefrigerated white shrimp (Litopenaeus vannamei) kept under modified atmospherepackaging. | J Food Sci | 2008 Apr | 18387125 |
| Role of sulfites and 4-hexylresorcinol in microbial growth and melanosisprevention of deepwater pink shrimp (Parapenaeus longirostris) using a controlledatmosphere. | J Food Prot | 2005 Jan | 15690809 |
| [Determination of 4-hexylresorcinol residues in prawns and crabs]. | Shokuhin Eiseigaku Zasshi | 2005 Dec | 16440790 |
| Influence of pH, benzoic acid, glutathione, EDTA, 4-hexylresorcinol, and sodiumchloride on the pressure inactivation kinetics of mushroom polyphenol oxidase. | J Agric Food Chem | 1999 Sep | 10552679 |
| 4-Hexylresorcinol as inhibitor of shrimp melanosis: efficacy and residues studies; evaluation of possible toxic effect in a human intestinal in vitro model (Caco-2); preliminary safety assessment. | Food Addit Contam | 1998 Feb-Mar | 9602923 |
Targets
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 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 ]
- Uniprot ID:
- P05184
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 ]
- General Function:
- Oxygen binding
- Specific Function:
- Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
- Gene Name:
- CYP19A1
- Uniprot ID:
- P11511
- Molecular Weight:
- 57882.48 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 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
- Gene Name:
- CYP2D6
- Uniprot ID:
- P10635
- Molecular Weight:
- 55768.94 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 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 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 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
- Gene Name:
- PPARG
- Uniprot ID:
- P37231
- Molecular Weight:
- 57619.58 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 ]
- General Function:
- Thromboxane a2 receptor activity
- Specific Function:
- Receptor for thromboxane A2 (TXA2), a potent stimulator of platelet aggregation. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol-calcium second messenger system. In the kidney, the binding of TXA2 to glomerular TP receptors causes intense vasoconstriction. Activates phospholipase C. Isoform 1 activates adenylyl cyclase. Isoform 2 inhibits adenylyl cyclase.
- Gene Name:
- TBXA2R
- Uniprot ID:
- P21731
- Molecular Weight:
- 37430.69 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 ]
- 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 ]