메틸파라벤

메틸파라벤
메틸파라벤 구조식 이미지
카스 번호:
99-76-3
한글명:
메틸파라벤
동의어(한글):
p-히드록시안식향산메틸;메틸파라벤;4-히드록시벤조산,메틸에스테르;4-히드록시벤조익액시드메틸에스테르;p-옥시안식향산메틸;P-히드록시벤조산,메틸에스테르;메틸P-옥시벤조에이트;메틸P-히드록시벤조에이트;메틸파라히드록시벤조에이트;메틸파라세프트;4-하이드록시안식향산메틸;메틸파라벤
상품명:
Methylparaben
동의어(영문):
METHYL 4-HYDROXYBENZOATE;Paraben;Methyl parahydroxybenzoate;NIPAGIN;METHYL P-HYDROXYBENZOATE;Nigagin;Solbrol;Nipagin M;4-HYDROXYBENZOIC ACID METHYL ESTER;Solbrol M
CBNumber:
CB0184566
분자식:
C8H8O3
포뮬러 무게:
152.15
MOL 파일:
99-76-3.mol
MSDS 파일:
SDS

메틸파라벤 속성

녹는점
125-128 °C (lit.)
끓는 점
298.6 °C
밀도
1,46g/cm
증기압
0.000005 hPa (20 °C)
굴절률
1.4447 (estimate)
FEMA
2710 | METHYL P-HYDROXYBENZOATE
인화점
280°C
저장 조건
room temp
용해도
에탄올: 용해성0.1M, 투명, 무색
산도 계수 (pKa)
pKa 8.15(H2O,t =20.0) (Uncertain)
물리적 상태
결정성 분말
색상
흰색에서 거의 흰색
수소이온지수(pH)
5.8 (H2O, 20°C) (saturated solution)
냄새
무취 또는 희미한 숯, 타는 냄새
수용성
물에 약간 용해됩니다.
어는점
131℃
Merck
14,6107
BRN
509801
안정성
안정적인. 강한 산화제, 강한 염기와 호환되지 않습니다.
InChIKey
LXCFILQKKLGQFO-UHFFFAOYSA-N
LogP
1.98 at 20℃
CAS 데이터베이스
99-76-3(CAS DataBase Reference)
NIST
Benzoic acid, 4-hydroxy-, methyl ester(99-76-3)
EPA
Methylparaben (99-76-3)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xi,Xn
위험 카페고리 넘버 36/37/38-20/21/22-36
안전지침서 26-36-24/25-39
유엔번호(UN No.) UN 2769
WGK 독일 1
RTECS 번호 DH2450000
자연 발화 온도 >600 °C
TSCA Yes
HS 번호 29182930
유해 물질 데이터 99-76-3(Hazardous Substances Data)
독성 LD50 orally in Rabbit: 2100 mg/kg
기존화학 물질 KE-20379
그림문자(GHS): GHS hazard pictograms
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H411 장기적 영향에 의해 수생생물에 유독함 수생 환경유해성 물질 - 만성 구분 2
예방조치문구:
P273 환경으로 배출하지 마시오.
P391 누출물을 모으시오.
P501 ...에 내용물 / 용기를 폐기 하시오.
NFPA 704
0
2 0

메틸파라벤 MSDS


4-Hydroxybenzoic acid methyl ester

메틸파라벤 C화학적 특성, 용도, 생산

순도시험

  (1) 융점 : 이 품목의 융점은 125~128℃이어야 한다.

  (2) 유리산 : 이 품목 0.75g에 물 15mL를 가하여 비등수욕 중에서 1분간 가열하고 식힌 다음 여과한 액은 산성 또는 중성이다. 여액 10mL를 취하여 0.1N 수산화나트륨용액 0.2mL 및 메틸레드시액 2방울을 가할 때, 그 액은 황색을 나타낸다.

  (3) 비소 : 이 품목을 비소시험법에 따라 시험할 때, 그 양은 4.0ppm 이하이어야 한다.

  (4) 납 : 이 품목 5.0g을 취하여 원자흡광광도법 또는 유도결합플라즈마발광광도법에 따라 시험할 때, 그 양은 2.0ppm 이하이어야 한다.

  (5) 파라옥시안식향산 및 살리실산 : 이 품목 약 0.5g을 에테르 30mL에 녹이고 탄산수소나트륨(1→100) 20mL를 가하여 섞은 후 물층을 분리한다. 물층을 에테르 20mL로 2회 씻은 다음 묽은황산 5mL 및 에테르 30mL을 가하여 섞은 후 에테르층을 분리하여 물 10mL을 가하여 섞고 여과한다. 소량의 에테르로 용기를 씻어서 여액과 합친 다음 수욕조에서 에테르를 증발시키고 잔류물을 황산데시케이터안에서 항량이 될 때까지 건조시킨다. 항량된 잔류물을 70℃의 물 25mL에 녹이고 묽은염화제이철시액 2~3방울을 가하였을 때 자~적자색이 나타나서는 아니 된다.

확인시험

  이 품목 0.5g에 수산화나트륨시액 10mL를 가하고 30분간 끓인 다음 증발 농축하여 약 5mL로 하고 식힌 다음 묽은황산으로 산성으로 하여 생성된 침전을 여취하여 물로 잘 씻고 105℃에서 1시간 건조할 때, 그 융점은 213~217℃이다.

정량법

  이 품목 약 2g을 정밀히 달아 이에 1N 수산화나트륨용액 40mL를 가하여 30분간 끓이고 식힌 다음 과잉의 알칼리를 1N 황산으로 적정한다(지시약 : 브로모티몰블루시액 5방울). 종말점의 색은 pH 6.5의 완충액에 같은 지시약을 가한 때의 색으로 한다. 따로 같은 방법으로 공시험을 한다.

1N 수산화나트륨용액 1mL = 152.2mg C8H8O3

강열잔류물

  이 품목 약 2g을 정밀히 달아 강열잔류물시험법에 따라 시험할 때, 그 양은 0.05% 이하이어야 한다.

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.

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.

정의

ChEBI: Methylparaben is a 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol. It is the most frequently used antimicrobial preservative in cosmetics. It occurs naturally in several fruits, particularly in blueberries. It has a role as a plant metabolite, an antimicrobial food preservative, a neuroprotective agent and an antifungal agent.

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.

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.

위험도

Toxic. Use in foods restricted to 0.1%.

Pharmaceutical Applications

Methylparaben is widely used as an antimicrobial preservative in cosmetics, food products, and pharmaceutical formulations; see Table I. It may be used either alone or in combination with other methylparaben is the most frequently used antimicrobial preservative.
The parabens are effective over a wide pH range and have a broad spectrum of antimicrobial activity, although they are most effective against yeasts and molds. Antimicrobial activity increases as the chain length of the alkyl moiety is increased, but aqueous solubility decreases; therefore a mixture of parabens is frequently used to provide effective preservation. Preservative efficacy is also improved by the addition of propylene glycol (2–5%), or by using parabens in combination with other antimicrobial agents such as imidurea;
Owing to the poor solubility of the parabens, paraben salts (particularly the sodium salt) are more frequently used in formulations. However, this raises the pH of poorly buffered formulations.
Methylparaben (0.18%) together with propylparaben (0.02%) has been used for the preservation of various parenteral pharmaceutical formulations;

색상 색인 번호

This substance is one of the parabens family. Parabens are esters formed by p-hydroxybenzoic acid and an alcohol. They are largely used as biocides in cosmetics and toiletries, medicaments, or food. They have synergistic power with other biocides. Parabens can induce allergic contact dermatitis, mainly in chronic dermatitis and wounded skin.

Carcinogenicity

The carcinogenic potential of methyl paraben has been studied in rodents. Several studies are available, but none that expose animals via oral or dermal routes. No evidence of a carcinogenic effect was observed following intravenous or subcutaneous injection .

저장

Aqueous solutions of methylparaben at pH 3–6 may be sterilized by autoclaving at 120°C for 20 minutes, without decomposition. Aqueous solutions at pH 3–6 are stable (less than 10% decomposition) for up to about 4 years at room temperature, while aqueous solutions at pH 8 or above are subject to rapid hydrolysis (10% or more after about 60 days storage at room temperature);
Methylparaben should be stored in a well-closed container in a cool, dry place.

Purification Methods

Fractionally crystallise the ester from its melt, and recrystallise it from *benzene, then from *benzene/MeOH and dry it over CaCl2 in a vacuum desiccator. [Beilstein 10 IV 360.]

비 호환성

The antimicrobial activity of methylparaben and other parabens is considerably reduced in the presence of nonionic surfactants, such as polysorbate 80, as a result of micellization.However, propylene glycol (10%) has been shown to potentiate the antimicrobial activity of the parabens in the presence of nonionic surfactants and prevents the interaction between methylparaben and polysorbate 80.
Incompatibilities with other substances, such as bentonite, magnesium trisilicate,talc,tragacanth,sodium alginate, essential oils,sorbitol,and atropine,have been reported. It also reacts with various sugars and related sugar alcohols. Absorption of methylparaben by plastics has also been reported; the amount absorbed is dependent upon the type of plastic and the vehicle. It has been claimed that low-density and high-density polyethylene bottles do not absorb methylparaben.
Methylparaben is discolored in the presence of iron and is subject to hydrolysis by weak alkalis and strong acids.

Regulatory Status

Methylparaben and propylparaben are affirmed GRAS Direct Food Substances in the USA at levels up to 0.1%. All esters except the benzyl ester are allowed for injection in Japan. In cosmetics, the EU and Brazil allow use of each paraben at 0.4%, but the total of all parabens may not exceed 0.8%. The upper limit in Japan is 1.0%.
Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (IM, IV, and SC injections; inhalation preparations; ophthalmic preparations; oral capsules, tablets, solutions and suspensions; otic, rectal, topical, and vaginal preparations). Included in medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

참고 문헌

The Protective Effect of Rosmarinic Acid against Unfavorable Influence of Methylparaben and Propylparaben on Collagen in Human Skin Fibroblasts DOI:10.3390/nu12051282
https://www.byrdie.com/methylparaben-for-skin-4779820
https://pubchem.ncbi.nlm.nih.gov/compound/Methylparaben
Handa O, et al. (2006). Methylparaben potentiates UV-induced damage of skin keratinocytes. DOI: 10.1016/j.tox.2006.07.018
Parabens in Cosmetics https://www.fda.gov/cosmetics/productsingredients/ingredients/ucm128042.htm
Okamoto T, et al. (2008). Combined activation of methyl paraben by light irradiation and metabolism toward oxidative DNA damage. DOI:10.1021/tx800066u

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