PROPYL p-HYDROXYBENZOATE
Relevant Data
Food Additives Approved in the United States
General Information
| Synonyms: | PROPYL p-OXYBENZOATE, PROPYLPARABEN |
| Chemical Names: | PROPYL p-HYDROXYBENZOATE; n-PROPYL ESTER OF p-HYDROXYBENZOIC ACID |
| CAS number: | 94-13-3 |
| FEMA number: | 2951 |
| INS: | 216 |
| Functional Class: |
Food Additives PRESERVATIVE |
From apps.who.int
Evaluations
| Evaluation year: | 2006 |
| ADI: | WITHDRAWN (2006) |
| Meeting: | 17 |
| Specs Code: | R (1995) |
| Comments: | In view of the adverse effects in male rats, propyl paraben (propyl p-hydroxybenzoate) should be excluded from the group ADI for the parabens used in food. This conclusion was reached on the grounds that the group ADI was originally set on a NOEL of 1000 mg/kg bw per day for a different toxicological end-point?growth depression?taken from the range of studies then available for the methyl, ethyl and propyl parabens. Propyl paraben has shown adverse effects in tissues of reproductive organs in male rats at dietary doses of down to 10 mg/kg bw per day, which is within the range of the group ADI (0?10 mg/kg bw), with no NOEL yet identified. |
| Report: | TRS 940-JECFA 67/30 |
| Tox Monograph: | FAS 58-JECFA 67 |
| Specification: | WITHDRAWN (2006); see FAO JECFA Monographs 3-JECFA 67/61 |
From apps.who.int
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 7175 |
| IUPAC Name | propyl 4-hydroxybenzoate |
| InChI | InChI=1S/C10H12O3/c1-2-7-13-10(12)8-3-5-9(11)6-4-8/h3-6,11H,2,7H2,1H3 |
| InChI Key | QELSKZZBTMNZEB-UHFFFAOYSA-N |
| Canonical SMILES | CCCOC(=O)C1=CC=C(C=C1)O |
| Molecular Formula | C10H12O3 |
| Wikipedia | propylparaben |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 180.203 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 4 |
| Complexity | 160.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B w 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 w A A A A A A A A A A A B A A A A G g A A C A A A D A S g m A I y D o A A B g C I A i D S C A A C A A A k I A A I i A E G C M g I J j K C N R q C c Q A k w B E I u Y e I 7 C z O I A A A 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 = = |
| Topological Polar Surface Area | 46.5 |
| Monoisotopic Mass | 180.079 |
| Exact Mass | 180.079 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| 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 |
From Pubchem
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8048 |
| Human Intestinal Absorption | HIA+ | 0.9955 |
| Caco-2 Permeability | Caco2+ | 0.8663 |
| P-glycoprotein Substrate | Non-substrate | 0.6327 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9050 |
| Non-inhibitor | 0.9572 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8374 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8806 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7784 |
| CYP450 2D6 Substrate | Non-substrate | 0.8839 |
| CYP450 3A4 Substrate | Non-substrate | 0.6157 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7756 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9119 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9411 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5806 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9631 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8925 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8877 |
| Non-inhibitor | 0.9354 | |
| AMES Toxicity | Non AMES toxic | 0.9686 |
| Carcinogens | Non-carcinogens | 0.8166 |
| Fish Toxicity | High FHMT | 0.6508 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9767 |
| Honey Bee Toxicity | High HBT | 0.7643 |
| Biodegradation | Ready biodegradable | 0.9390 |
| Acute Oral Toxicity | III | 0.8523 |
| Carcinogenicity (Three-class) | Non-required | 0.5469 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.3823 | LogS |
| Caco-2 Permeability | 1.2293 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8885 | LD50, mol/kg |
| Fish Toxicity | 1.1549 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.2617 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | None |
|---|---|
| Mechanism of Toxicity | None |
| Metabolism | None |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | None |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzoic acids and derivatives |
| Intermediate Tree Nodes | Benzoic acid esters - p-Hydroxybenzoic acid esters |
| Direct Parent | p-Hydroxybenzoic acid alkyl esters |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | P-hydroxybenzoic acid alkyl ester - Benzoyl - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group. |
From ClassyFire
Targets
- 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 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 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
- Pereira-Fernandes A, Demaegdt H, Vandermeiren K, Hectors TL, Jorens PG, Blust R, Vanparys C: Evaluation of a screening system for obesogenic compounds: screening of endocrine disrupting compounds and evaluation of the PPAR dependency of the effect. PLoS One. 2013 Oct 14;8(10):e77481. doi: 10.1371/journal.pone.0077481. eCollection 2013. [24155963 ]
From T3DB