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바닐린

바닐린
바닐린 구조식 이미지
카스 번호:
121-33-5
한글명:
바닐린
동의어(한글):
바닐린;바닐알데히드;4-히드록시-3-메톡시벤즈알데히드;P-바닐린;파라-바닐린
상품명:
Vanillin
동의어(영문):
Zimco;Lioxin;Vanilin;VANILLA;VANILLIN;Vinillin;Rhovanil;VANILLINE;FEMA 3107;VANILLINUM
CBNumber:
CB8262475
분자식:
C8H8O3
포뮬러 무게:
152.15
MOL 파일:
121-33-5.mol

바닐린 속성

녹는점
81-83 °C(lit.)
끓는 점
170 °C15 mm Hg(lit.)
밀도
1.06
증기 밀도
5.3 (vs air)
증기압
>0.01 mm Hg ( 25 °C)
굴절률
1.4850 (estimate)
FEMA
3107 | VANILLIN
인화점
147 °C
저장 조건
Refrigerator
용해도
methanol: 0.1 g/mL, clear
산도 계수 (pKa)
pKa 7.396±0.004(H2O I = 0.00 t = 25.0±1.0) (Reliable)
물리적 상태
Crystalline Powder
색상
White to pale yellow
수소이온지수(pH)
4.3 (10g/l, H2O, 20℃)
수용성
10 g/L (25 ºC)
감도
Air & Light Sensitive
Merck
14,9932
JECFA Number
889
BRN
472792
안정성
Stable. May discolour on exposure to light. Moisture-sensitive. Incompatible with strong oxidizing agents, perchloric acid.
CAS 데이터베이스
121-33-5(CAS DataBase Reference)
NIST
Benzaldehyde, 4-hydroxy-3-methoxy-(121-33-5)
EPA
Benzaldehyde, 4-hydroxy-3-methoxy-(121-33-5)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn,Xi
위험 카페고리 넘버 22-36/37/38-36
안전지침서 24/25-22-37/39-26-36/37/39
유엔번호(UN No.) UN 2924 3/8/PG II
WGK 독일 1
RTECS 번호 YW5775000
자연 발화 온도 >400 °C
TSCA Yes
위험 등급 3/8
포장분류 II
HS 번호 29124100
유해 물질 데이터 121-33-5(Hazardous Substances Data)
독성 LD50 orally in rats, guinea pigs: 1580, 1400 mg/kg (Jenner)
그림문자(GHS):
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H332 흡입하면 유해함 급성 독성 물질 흡입 구분 4 경고 P261, P271, P304+P340, P312
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

바닐린 MSDS


4-Hydroxy-3-methoxybenzaldehyde

바닐린 C화학적 특성, 용도, 생산

물성

바닐린은 페놀 알데하이드, 분자 공식 C8H8O3를 가진 유기화합물입니다. 그것의 작용기는 알데하이드, 에테르 및 석탄산을 포함합니다. 바닐린은 바닐라 콩의 추출물의 1 차적인 성분입니다.
바닐린의 가장 큰 사용은 감미로운 음식에서 flavoring로, 보통 입니다. 아이스크림과 초콜렛 공업은 적은 양이 flavoring로 바닐린을 위한 시장을 함께 75%를, 과자와 구워진 상품에서 사용된 상태에서 함유합니다.
바닐린은 또한 많은 다른 풍미를 위해 아주 중요한 중요한 주로 풍미 공업에서, 특히 크림 같은 단면도 사용됩니다.
바닐린은 조제약과 다른 사람의 생산에 있는 화학물질 중간물로 벌금 화학물질 사용되었습니다.

생산/준비/합성

① 리그닌에서의 제조: 펄프 공업의 폐액 속에 함유된 리그닌 설폰산을 알칼리와 산화구리 또는 니트로벤젠으로 산화하여 리그닌바닐린을 얻는다.
② 구아야콜에서의 제조 : 구아야콜과 클로로포름 또는 클로랄을 알칼리 존재하에서 축합시키고(라이머-티만 반응), 이것을 산화시켜 합성한다.
③ 이 밖에 유제놀 또는 트리포린을 원료로 하는 방법도 있다.
또한 바닐린 분자속의 -OCH기(基) 대신에 -OCH기가 들어간 것이 합성되어 바닐린과 같은 방향을 가지고 또 그 강도도 강한 것이 나타나게 되었다.
이것을 에틸바닐린 또는 부르보날(bourbonal)이라고 한다.
바닐린에 비해 착색되지 않으므로 착색을 싫어하는 제품에 바닐린과 같은 용도, 달콤한 꽃향, 과일향 등 조합향료로 널리 사용된다.

용도

그것은 화장품 것과 같이 그리고 고무, 플라스틱 및 다른 제품의 향수를 바르기에서 제과, 아이스크림, 음료, 케이크, 초콜렛, 빵, 건빵, 담배, 포도주 및 사료 우물에서 널리 이용됩니다. 그것은 또한 약에서 사용되고, 그리고 다른 기업 그리고 화학 시약으로 사용해 전기도금을 합니다.

화학적 성질

White, crystalline needles; sweetish smell. Soluble in 125 parts water, in 20 parts glycerol, and in 2 parts 95% alcohol; soluble in chloroform and ether. Combustible.

화학적 성질

White or cream, crystalline needles or powder with characteristic vanilla odor and sweet taste.

화학적 성질

Vanillin is found in many essential oils and foods but is often not essential for their odor or aroma. However, it does determine the odor of essential oils and extracts from Vanilla planifolia and Vanilla tahitensis pods, in which it is formed during ripening by enzymatic cleavage of glycosides.
Vanillin is a colorless, crystalline solid (mp 82–83°C) with a typical vanilla odor. Because it possesses aldehyde and hydroxy substituents, it undergoes many reactions. Additional reactions are possible due to the reactivity of the aromatic nucleus. Vanillyl alcohol and 2-methoxy-4-methylphenol are obtained by catalytic hydrogenation; vanillic acid derivatives are formed after oxidation and protection of the phenolic hydroxy group. Since vanillin is a phenol aldehyde, it is stable to autoxidation and does not undergo the Cannizzaro reaction. Numerous derivatives can be prepared by etherification or esterification of the hydroxy group and by aldol condensation at the aldehyde group. Several of these derivatives are intermediates, for example, in the synthesis of pharmaceuticals.

화학적 성질

A great variety of vanilla plants bearing the vanilla pods, or siliques, exist. Those mentioned above are the most important species. Of special value are those cultivated in Mexico, Madagascar, Java, Tahiti, the Comoro Islands and Réunion. The cultivation of vanilla beans is very long and laborious. The plant is a perennial herbaceous vine that grows up to 25 m in height and needs suitable supports in order to grow. Fecundation of flowers is performed (November to December) by perforating the membrane that separates the pollen from the pistil. This is an exacting task requiring skilled hand labor. Natural fecundation occurs when a similar operation is carried out by birds or insects that perforate the membrane in search of food. After a few months, clusters of hanging pods (siliques) are formed; these start to yellow at the lower tip from August to September. At this point, the siliques are harvested and undergo special treatment that develops the aroma. The siliques are placed in straw baskets and dipped into hot water to rupture the inner cell wall. After a few months, the aroma starts developing. Then the siliques are exuded by intermittent exposure to sunlight (by alternately covering and uncovering the siliques with wool blankets). When exudation is complete, the siliques are oiled with cocoa oil to avoid chapping during drying and are finally dried to a suitable residual moisture content. In the final stage of the preparation, the best quality siliques form a vanilla “brine” that crystallizes on the surface of the bean. Generally, the processing of vanilla bean takes more than a year. The most important commercial qualities are brined vanilla, bastard vanilla and vanilla pompona. The bean is the only part used. Vanilla has a sweet, ethereal odor and characteristic flavor.

화학적 성질

Vanillin has a characteristic, creamy, vanilla-like odor with a very sweet taste.

출처

Vanillin occurs widely in nature; it has been reported in the essential oil of Java citronella (Cymbopogon nardus Rendl.), in benzoin, Peru balsam, clove bud oil and chiefly vanilla pods (Vanilla planifolia, V. tahitensis, V. pompona); more that 40 vanilla varieties are cultivated; vanillin is also present in the plants as glucose and vanillin. Reported found in guava, feyoa fruit, many berries, asparagus, chive, cinnamon, ginger, Scotch spearmint oil, nutmeg, crisp and rye bread, butter, milk, lean and fatty fish, cured pork, beer, cognac, whiskies, sherry, grape wines, rum, cocoa, coffee, tea, roast barley, popcorn, oatmeal, cloudberry, passion fruit, beans, tamarind, dill herb and seed, sake, corn oil, malt, wort, elderberry, loquat, Bourbon and Tahiti vanilla and chicory root.

용도

Vanillin is a flavorant made from synthetic or artificial vanilla which can be derived from lignin of whey sulfite liquors and is syntheti- cally processed from guaiacol and eugenol. the related product, ethyl vanillin, has three and one-half times the flavoring power of vanillin. vanillin also refers to the primary flavor ingredient in vanilla, which is obtained by extraction from the vanilla bean. vanillin is used as a substitute for vanilla extract, with application in ice cream, desserts, baked goods, and beverages at 60–220 ppm.

용도

An intermediate and analytical reagent.

용도

Pharmaceutic aid (flavor). As a flavoring agent in confectionery, beverages, foods and animal feeds. Fragance and flavor in cosmetics. Reagent for synthesis. Source of L-dopa.

용도

The primary component of Vanilla bean extract.

용도

Labelled Vanillin. Occurs naturally in a wide variety of foods and plants such as orchids; major commercial source of natural vanillin is from vanilla bean extract. Synthetically produced in-bulk fro m lignin-based byproduct of paper processes or from guaicol.

정의

ChEBI: A member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively.

제조 방법

Commercial vanillin is obtained by processing waste sulfite liquors or is synthesized from guaiacol. Preparation by oxidation of isoeugenol is of historical interest only.
1) Preparation from waste sulfite liquors: The starting material for vanillin production is the lignin present in sulfite wastes from the cellulose industry. The concentrated mother liquors are treated with alkali at elevated temperature and pressure in the presence of oxidants. The vanillin formed is separated from the by-products, particularly acetovanillone (4-hydroxy-3- methoxyacetophenone), by extraction, distillation, and crystallization. A large number of patents describe various procedures for the (mainly) continuous hydrolysis and oxidation processes, as well as for the purification steps required to obtain high-grade vanillin . Lignin is degraded either with sodium hydroxide or with calcium hydroxide solution and simultaneously oxidized in air in the presence of catalysts. When the reaction is completed, the solid wastes are removed. Vanillin is extracted from the acidified solutionwith a solvent (e.g., butanol or benzene) and reextractedwith sodium hydrogen sulfite solution. Reacidification with sulfuric acid followed by vacuum distillation yields technical-grade vanillin, which must be recrystallized several times to obtain food-grade vanillin.Water, to which some ethanol may be added, is used as the solvent in the last crystallization step.
2) Preparation from guaiacol: Severalmethods can be used to introduce an aldehyde group into an aromatic ring. Condensation of guaiacol with glyoxylic acid followed by oxidation of the resulting mandelic acid to the corresponding phenylglyoxylic acid and, finally, decarboxylation continues to be a competitive industrial process for vanillin synthesis.
a. Vanillin from guaiacol and glyoxylic acid: Currently, guaiacol is synthesized from catechol, which is mainly prepared by acid-catalyzed hydroxylation of phenol with hydrogen peroxide. In China, a guaiacol prepared from o-nitrochlorobenzene via o-anisidine is also used. Glyoxylic acid is obtained as a by-product in the synthesis of glyoxal from acetaldehyde and can also be produced by oxidation of glyoxal with nitric acid. Condensation of guaiacol with glyoxylic acid proceeds smoothly at room temperature and in weakly alkaline media. A slight excess of guaiacol is maintained to avoid formation of disubstituted products; excess guaiacol is recovered. The alkaline solution containing 4-hydroxy- 3-methoxymandelic acid is then oxidized in air in the presence of a catalyst until the calculated amount of oxygen is consumed [358]. Crude vanillin is obtained by acidification and simultaneous decarboxylation of the (4-hydroxy-3-methoxyphenyl)glyoxylic acid solution.
This process has the advantage that, under the reaction conditions, the glyoxyl radical enters the aromatic guaiacol ring almost exclusively para to the phenolic hydroxy group. Tedious separation procedures are thus avoided. b. Vanillin from guaiacol and formaldehyde: An older process that is still in use consists of the reaction of guaiacolwith formaldehyde or formaldehyde precursors such as urotropine, N,N-dimethyl-aniline, and sodium nitrite .

생산 방법

Vanillin occurs naturally in many essential oils and particularly in the pods of Vanilla planifolia and Vanilla tahitensis. Industrially, vanillin is prepared from lignin, which is obtained from the sulfite wastes produced during paper manufacture. Lignin is treated with alkali at elevated temperature and pressure, in the presence of a catalyst, to form a complex mixture of products from which vanillin is isolated. Vanillin is then purified by successive recrystallizations.
Vanillin may also be prepared synthetically by condensation, in weak alkali, of a slight excess of guaiacol with glyoxylic acid at room temperature. The resultant alkaline solution, containing 4- hydroxy-3-methoxymandelic acid is oxidized in air, in the presence of a catalyst, and vanillin is obtained by acidification and simultaneous decarboxylation. Vanillin is then purified by successive recrystallizations.

Composition

In addition to vanillin (approximately 3%), vanilla contains other aromatic principles: vanillin, piperonal, eugenol, glucovanillin, vanillic acid, anisic acid and anisaldehyde. Although vanillin is associated with the characteristic fragrance of the plant, the quality of vanilla bean is not associated with the vanillin content. Bourbon beans contain a high amount of vanillin compared to Mexican and Tahiti beans.

Aroma threshold values

Detection: 29 ppb to 1.6 ppm; recognition: 4 ppm

Taste threshold values

Taste characteristics at 10 ppm: sweet, typical vanilla-like, marshmallow, creamy-coumarin, caramellic with a powdery nuance.

공기와 물의 반응

Slowly oxidizes on exposure to air. . Slightly water soluble.

반응 프로필

Vanillin can react violently with Br2, HClO4, potassium-tert-butoxide, (tert-chloro-benzene + NaOH), (formic acid + Tl(NO3)3). . Vanillin is an aldehyde. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction).

화재위험

Flash point data for Vanillin are not available, however Vanillin is probably combustible.

Pharmaceutical Applications

Vanillin is widely used as a flavor in pharmaceuticals, foods, beverages, and confectionery products, to which it imparts a characteristic taste and odor of natural vanilla. It is also used in perfumes, as an analytical reagent and as an intermediate in the synthesis of a number of pharmaceuticals, particularly methyldopa. Additionally, it has been investigated as a potential therapeutic agent in sickle cell anemia and is claimed to have some antifungal properties.
In food applications, vanillin has been investigated as a preservative.
As a pharmaceutical excipient, vanillin is used in tablets, solutions (0.01–0.02% w/v), syrups, and powders to mask the unpleasant taste and odor characteristics of certain formulations, such as caffeine tablets and polythiazide tablets. It is similarly used in film coatings to mask the taste and odor of vitamin tablets. Vanillin has also been investigated as a photostabilizer in furosemide 1% w/v injection, haloperidol 0.5% w/v injection, and thiothixene 0.2% w/v injection.

Safety Profile

Moderately toxic by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Experimental reproductive effects. Human mutation data reported. Can react violently with Br2, HClO4, potassium-tert-butoxide, tert- chlorobenzene + NaOH, formic acid + thallium nitrate. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.

Safety

There have been few reports of adverse reactions to vanillin, although it has been speculated that cross-sensitization with other structurally similar molecules, such as benzoic acid, may occur.
Adverse reactions that have been reported include contact dermatitis and bronchospasm caused by hypersensitivity.
The WHO has allocated an estimated acceptable daily intake for vanillin of up to 10 mg/kg body-weight.
LD50 (guinea pig, IP): 1.19 g/kg
LD50 (guinea pig, oral): 1.4 g/kg
LD50 (mouse, IP): 0.48 g/kg
LD50 (rat, IP): 1.16 g/kg
LD50 (rat, oral): 1.58 g/kg
LD50 (rat, SC): 1.5 g/kg

Chemical Synthesis

From the waste (liquor) of the wood-pulp industry; vanillin is extracted with benzene after saturation of the sulfite waste liquor with CO2. Vanillin is also derived naturally through fermentation.

저장

Vanillin oxidizes slowly in moist air and is affected by light.
Solutions of vanillin in ethanol decompose rapidly in light to give a yellow-colored, slightly bitter tasting solution of 6,6’-dihydroxy- 5,5’-dimethoxy-1,1’-biphenyl-3,3’-dicarbaldehyde. Alkaline solutions also decompose rapidly to give a brown-colored solution. However, solutions stable for several months may be produced by adding sodium metabisulfite 0.2% w/v as an antioxidant.
The bulk material should be stored in a well-closed container, protected from light, in a cool, dry place.

Purification Methods

Crystallise vanillin from water or aqueous EtOH, or by distillation in vacuo.[Beilstein 8 IV 1763.]

비 호환성

Incompatible with acetone, forming a brightly colored compound. A compound practically insoluble in ethanol is formed with glycerin.

Regulatory Status

GRAS listed. Included in the FDA Inactive Ingredients Database (oral solutions, suspensions, syrups, and tablets). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

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