WordNet
- the univalent radical CH3- derived from methane (同)methyl_group, methyl radical
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/16 21:41:41」(JST)
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Methylparaben
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| Names |
| IUPAC name
Methyl 4-hydroxybenzoate
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Other names
Methyl paraben;
Methyl p-hydroxybenzoate;
Methyl parahydroxybenzoate;
Nipagin M;
E number E218; Tegosept; Mycocten |
| Identifiers |
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CAS Number
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99-76-3 Y |
| ChEBI |
CHEBI:31835 N |
| ChEMBL |
ChEMBL325372 Y |
| ChemSpider |
7176 Y |
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IUPHAR/BPS
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6273 |
| Jmol 3D model |
Interactive image |
| KEGG |
D01400 Y |
| PubChem |
7456 |
| UNII |
A2I8C7HI9T Y |
InChI
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InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 Y
Key: LXCFILQKKLGQFO-UHFFFAOYSA-N Y
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InChI=1/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3
Key: LXCFILQKKLGQFO-UHFFFAOYAH
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| Properties |
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Chemical formula
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C8H8O3 |
| Molar mass |
152.15 g·mol−1 |
| Appearance |
Colorless crystals or white crystalline powder [1] |
| UV-vis (λmax) |
255 nm (methanol) |
| Hazards |
| NFPA 704 |
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| Related compounds |
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Related Parabens
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Ethylparaben
Propylparaben
Butylparaben |
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Related compounds
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Methyl salicylate (ortho isomer) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is YN ?) |
| Infobox references |
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UV-visible spectrum of methylparaben
Methylparaben, also methyl paraben, one of the parabens, is a preservative with the chemical formula CH3(C6H4(OH)COO). It is the methyl ester of p-hydroxybenzoic acid.
Contents
- 1 Natural occurrences
- 2 Uses
- 3 Safety
- 4 References
- 5 External links
Natural occurrences
Methylparaben serves as a pheromone for a variety of insects[2] and is a component of queen mandibular pheromone. Some plants produce methylparaben, example thale cress.[3] It is commonly used in the preparation of liquid dosage forms.
Uses
Methylparaben is an anti-fungal agent often used in a variety of cosmetics and personal-care products. It is also used as a food preservative and has the E number E218.
Methylparaben is commonly used as a fungicide in Drosophila food media. To Drosophila, methylparaben is toxic at higher concentrations, has an estrogenic effect, and slows the growth rate in the larval and pupal stages at lower concentrations.[4]
Safety
There is controversy about whether methylparaben or propylparabens are harmful at concentrations typically used in body care or cosmetics. Methylparaben and propylparaben are considered generally recognized as safe (GRAS) for food and cosmetic antibacterial preservation.[5] Methylparaben is readily metabolized by common soil bacteria, making it completely biodegradable.
Methylparaben is readily absorbed from the gastrointestinal tract or through the skin.[6] It is hydrolyzed to p-hydroxybenzoic acid and rapidly excreted in urine without accumulating in the body.[6] Acute toxicity studies have shown that methylparaben is practically non-toxic by both oral and parenteral administration in animals.[6] In a population with normal skin, methylparaben is practically non-irritating and non-sensitizing; however, allergic reactions to ingested parabens have been reported.[6]
Studies indicate that methylparaben applied on the skin may react with UVB, leading to increased skin aging and DNA damage.[7][8]
References
- ^ https://pubchem.ncbi.nlm.nih.gov/compound/Methyl_4-hydroxybenzoate#section=Experimental-Properties
- ^ Semiochemical - me-4-hydroxybenzoate, pherobase.com
- ^ Walker TS, Bais HP, Halligan KM, Stermitz FR, Vivanco JM (2003). "Metabolic profiling of root exudates of Arabidopsis thaliana". Journal of Agricultural and Food Chemistry 51 (9): 2548–54. doi:10.1021/jf021166h. PMID 12696935.
- ^ Gu Wei (2009). "Toxicity and Estrogen Effects of Methyl Paraben on Drosophila melanogaster". Food Science 30 (1): 252–254.
- ^ Parabens, Food and Drug Administration
- ^ a b c d Soni MG, Taylor SL, Greenberg NA, Burdock GA (2002). "Evaluation of the health aspects of methyl paraben: a review of the published literature". Food and Chemical Toxicology 40 (10): 1335–73. doi:10.1016/S0278-6915(02)00107-2. PMID 12387298.
- ^ Handa, O; Kokura, S; Adachi, S; Takagi, T; Naito, Y; Tanigawa, T; Yoshida, N; Yoshikawa, T (2006). "Methylparaben potentiates UV-induced damage of skin keratinocytes". Toxicology 227 (1–2): 62–72. doi:10.1016/j.tox.2006.07.018. PMID 16938376.
- ^ Okamoto, Yoshinori; Hayashi, Tomohiro; Matsunami, Shinpei; Ueda, Koji; Kojima, Nakao (2008). "Combined Activation of Methyl Paraben by Light Irradiation and Esterase Metabolism toward Oxidative DNA Damage". Chemical Research in Toxicology 21 (8): 1594–9. doi:10.1021/tx800066u. PMID 18656963.
External links
- Methylparaben at Hazardous Substances Data Bank
- Methylparaben at Household Products Database
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Phenolic acids (C6-C1) and their glycosides
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| Monohydroxybenzoic acids |
- 3-Hydroxybenzoic acid
- 4-Hydroxybenzoic acid
- Salicylic acid (2-Hydroxybenzoic acid)
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Glycosides
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- p-Hydroxybenzoic acid glucoside
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Acetylated
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- Methylparaben (Methyl p-hydroxybenzoic acid)
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| Dihydroxybenzoic acids |
- 2,3-Dihydroxybenzoic acid (Hypogallic acid)
- 2,4-Dihydroxybenzoic acid
- 2,5-Dihydroxybenzoic acid (Gentisic acid)
- 2,6-Dihydroxybenzoic acid
- 3,4-Dihydroxybenzoic acid (Protocatechuic acid)
- 3,5-Dihydroxybenzoic acid
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Acetylated
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- Ethyl protocatechuate
- Orsellinic acid
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| Trihydroxybenzoic acids |
- Gallic acid
- Phloroglucinol carboxylic acid
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Glycosides
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- Bergenin
- Norbergenin
- Theogallin
- Chebulic acid
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Acetylated
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- Ethyl gallate
- Eudesmic acid
- Methyl gallate
- Syringic acid
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UpToDate Contents
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English Journal
- Development and Validation of a Stability Indicating RP-HPLC Method for Hydrocortisone Acetate Active Ingredient, Propyl Parahydroxybenzoate and Methyl Parahydroxybenzoate Preservatives, Butylhydroxyanisole Antioxidant, and Their Degradation Products in a Rectal Gel Formulation.
- Ascaso M1, Pérez-Lozano P, García M, García-Montoya E, Miñarro M, Ticó JR, Fàbregas A, Carrillo C, Sarrate R, Suñé-Negre JM.
- Journal of AOAC International.J AOAC Int.2015 Jan-Feb;98(1):27-34. doi: 10.5740/jaoacint.13-411.
- A stability indicating method was established through a stress study, wherein different methods of degradation (oxidation, hydrolysis, photolysis, and temperature) were studied simultaneously to determine the active ingredient hydrocortisone acetate, preservatives propyl parahydroxybenzoate, and met
- PMID 25857875
- Retinal vascular occlusion after vitrectomy with retrobulbar anesthesia-observational case series and survey of literature.
- Tappeiner C1, Garweg JG.
- Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv für klinische und experimentelle Ophthalmologie.Graefes Arch Clin Exp Ophthalmol.2011 Dec;249(12):1831-5. doi: 10.1007/s00417-011-1783-9. Epub 2011 Aug 18.
- BACKGROUND: Severe postoperative loss of vision has been occasionally reported as a rare complication of retrobulbar anesthesia, and several possible causes have been proposed in the literature. In this work, our own and other investigators' experiences with these complications are surveyed with a v
- PMID 21850439
- Use of 8-substituted-FAD analogues to investigate the hydroxylation mechanism of the flavoprotein 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase.
- Chaiyen P1, Sucharitakul J, Svasti J, Entsch B, Massey V, Ballou DP.
- Biochemistry.Biochemistry.2004 Apr 6;43(13):3933-43.
- 2-Methyl-3-hydroxypyridine-5-carboxylic acid (MHPC) oxygenase (MHPCO) is a flavoprotein that catalyzes the oxygenation of MHPC to form alpha-(N-acetylaminomethylene)-succinic acid. Although formally similar to the oxygenation reactions catalyzed by phenol hydroxylases, MHPCO catalyzes the oxygenatio
- PMID 15049701
Japanese Journal
- 熱測定 : netsu = Calorimetry and thermal analysis 25(4), 111-116, 1998-09-30
- NAID 10001985188
- Studies on the Dissolution Behavior of Doxorubicin Hydrochloride Freeze-Dried Product
- Studies on the dissolution behavior of doxorubicin hydrochloride freeze-dried product.
Related Links
- Sigma-Aldrich offers Sigma-Aldrich-M1650000, Methyl parahydroxybenzoate for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... General description This product is provided ...
- [1] Parabens, Food and Drug Administration. [2] Soni MG, Taylor SL, Greenberg NA, Burdock GA (October 2002). "Evaluation of the health aspects of methyl paraben: a review of the published literature". Food Chem. Toxicol. 40 (10 ...
Related Pictures
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- 英
- methyl parahydroxybenzoate
