메틸파라벤
p-히드록시안식향산메틸 · 메틸파라벤 · 4-히드록시벤조산,메틸에스테르 · 4-히드록시벤조익액시드메틸에스테르 · p-옥시안식향산메틸 · P-히드록시벤조산,메틸에스테르 · 메틸P-옥시벤조에이트 · 메틸P-히드록시벤조에이트
식별자 및 물리적 특성
| CAS No. | 99-76-3 |
|---|---|
| 분자식 | C8H8O3 |
| 평균 분자량 | 152.15 g/mol |
| 단동위원소 질량 | 152.04734412 g/mol |
| SMILES | COC(=O)c1ccc(O)cc1 |
| InChIKey | LXCFILQKKLGQFO-UHFFFAOYSA-N |
| PubChem CID | 7456 |
| ChEMBL | CHEMBL325372 |
| ChEBI | CHEBI:31835 |
| EC No. | 202-785-7 |
| DTXSID | DTXSID4022529 |
| 현지명 | 메틸파라벤 |
화학 및 물리적 성질
| XLogP | 2 |
|---|---|
| 극성 표면적 | 46.5 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 136 |
| 물질 분류 | Other Uses -> Preservatives |
| 화장품 | Cosmetics ingredient -> ColorantFragrancePreservative/StabilizerCosmetic ingredients (Methylparaben) -> CIR (Cosmetic Ingredient Review) |
| SpringerMaterials Properties | Boiling point |
| 향료 | Fragrance Ingredient (Methyl p-hydroxybenzoate) -> IFRA transparency List |
| 농약 | Agrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: Not approvedBiocide |
| LogP(분배 계수) | log Kow = 1.96 |
| 냄새 | Odorless or has faint characteristic odor무취 또는 희미한 숯, 타는 냄새 |
| 맛 | Slight burning taste |
| 식품 첨가물 | ANTIMICROBIAL AGENT, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Color/Form | White needlesColorless crystals or white crystalline powderNeedles from dil alcohol |
| 용해도 | In water, 2.50X10+3 mg/L at 25 °CSolubility in water (w/w): 0.25% at 20 °C0.30% at 25 °CSolubilities in various solvents[Table#2967]Slightyl soluble in watervery soluble in ethanol, ether, acetonesoluble in trfluoroacetic acidFor more Solubility (Complete) data for METHYLPARABEN (6 total), please visit the HSDB record page.2.5 mg/mL at 25 °C에탄올: 용해성0.1M, 투명, 무색 |
| Animal Drugs | Pharmaceuticals -> UK Veterinary Medicines Directorate List |
| 녹는점 | 125-128 °C (lit.) |
| 끓는 점 | 298.6 °C |
| 밀도 | 1,46g/cm |
| 증기압 | 0.000005 hPa (20 °C) |
| FEMA | 2710 | METHYL P-HYDROXYBENZOATE |
| 굴절률 | 1.4447 (estimate) |
| 인화점 | 280°C |
| 저장 조건 | room temp |
| pKa(산도 계수) | pKa 8.15(H2O,t =20.0) (Uncertain) |
| 물리적 상태 | 결정성 분말 |
| 색상 | 흰색에서 거의 흰색 |
| pH | 5.8 (H2O, 20°C) (saturated solution) |
| 생물학적 소스 | synthetic |
| 용해도 | 물에 약간 용해됩니다. |
| Merck | 14,6107 |
| BRN | 509801 |
| 헨리 상수 | 4.5×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| 안정성 | 안정적인. 강한 산화제, 강한 염기와 호환되지 않습니다. |
| 주요 응용 | 향료 및 향 |
| 화장품 원료 기능 | 항균 방부제향기 |
| InChI | 1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 |
| InChIKey | LXCFILQKKLGQFO-UHFFFAOYSA-N |
| SMILES | COC(=O)c1ccc(O)cc1 |
| LogP(분배 계수) | 1.98 at 20℃ |
| NIST | Benzoic acid, 4-hydroxy-, methyl ester(99-76-3) |
| EPA | Methylparaben (99-76-3) |
화학적 성질
Methylparaben occurs as colorless crystals or a white crystalline powder. It is odorless or almost odorless and has a slight burning taste. Soluble in alcohol,ether; slightly soluble in water, benzene, and carbontetrachloride.
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 31.5% (1035 of 3282) of reports.WarningH315 (53.8%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3282 reports by companies from 32 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Chemical: Benzoic acid, 4-hydroxy-, methyl esterHazard Traits - Endocrine ToxicityReproductive ToxicityDirective (EC) No 114/2003Benzoic acid, 4-hydroxy-, methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, 4-hydroxy-, methyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)2007/442Status: Active Update: 19-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14310 |
| 기타 안전 정보 | IMAP assessments - Parabens: Human health tier II assessment |
| 유해성 요약 | Parabens are an uncommon cause of allergic contact dermatitis[Marks, p. 115] Food use limited to 0.1%[Hawley] Observations from animal studies include mild skin and eye irritation and a low order of toxicity in high-dose oral studiesSkin sensitization has been reported from cosmetics and topical medicationsA moderate eye irritant (saturated aqueous solution)Practically non-toxic in animal studies: Oral LD50 (mouse) >8000 mg/kg (Effects included flaccid paralysis and ataxia.)[HSDB] An eye and mild skin irritantMay cause skin sensitization[eChemPortal: ERMA] Parabens can induce allergic contact dermatitis, mainly in chronic dermatitis and wounded skin. [Kanerva, p. 1822-3] An irritant[MSDSonline] |
| FDA 요건 | Methylparaben is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part. |
용도
출처
Reported present in cloudberry, yellow passion fruit juice, white wine, botrytised wine and Bourbon vanilla.
용도
Methylparaben and propylparaben are the most common of these. parabens is one of the most commonly used group of preservatives in the cosmetic, pharmaceutical, and food industries. Parabens provide bacteriostatic and fungistatic activity against a diverse number of organisms, and are considered safe for use in cosmetics, particularly in light of their low sensitizing potential. An evaluation of preservatives for use in leave-on cosmetic preparations lists parabens among the least sensitizing. The range of concentrations used in cosmetics varies between 0.03 and 0.30 percent, depending on the conditions for use and the product to which the paraben is added.Methylparaben is one of the most popular preservatives in beauty products and food items. According to the National Library of Medicine, the ingredient occurs naturally in a handful of fruits—like blueberries—though it can also be created synthetically.It's found in everything from cream cleansers and moisturizers to primers and foundations and helps these products maintain their effectiveness. Rabach says that it's chock-full of anti-fungal and antibacterial properties, which work wonders to extend the shelf life of skincare, haircare, and cosmetic products.
일반 설명
Methyl paraben is basically a methyl ester of p-hydroxybenzoic acid. It is non-toxic, and non-carcinogenic in nature. It is a stable, non-volatile compound and finds application as an anti-microbial preservative in foods, drugs and cosmetics. It is readily absorbed through the skin and gastrointestinal tract. Upon hydrolyzation, it is hydrolyzed to p-hydroxybenzoic acid, and the conjugates formed get rapidly excreted in the urine.
제조 및 합성 방법
제조 방법
Methylparaben is produced through the methanol esterification of p-hydroxybenzoic acid in the presence of sulfuric acid. The materials are heated in a glass-lined reactor and distilled under reflux. The resulting acid is neutralized with caustic soda, then crystallized through cooling. The crystallized product is centrifuged, washed, dried under vacuum, milled and blended, all in corrosion-resistant equipment to avoid metallic contamination.