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말레익산

말레익산
말레익산 구조식 이미지
카스 번호:
6915-15-7
한글명:
말레익산
동의어(한글):
말산;말레익산;사과산;하이드록시숙신산;말산(MALICACID);2-하이드록시숙신 산;2-하이드록시숙신산;데옥시테트라르 산;말 산;숙신산, 하이드록시;알파-하이드록시숙신 산;포말 산;말릭애씨드
상품명:
Malic acid
동의어(영문):
-MaL;malic;E 296;DL-Malic;FDA 2018;malicaci;DL-MALATE;NSC 25941;MALIC ACID;pomalusacid
CBNumber:
CB7220795
분자식:
C4H6O5
포뮬러 무게:
134.09
MOL 파일:
6915-15-7.mol

말레익산 속성

녹는점
131-133 °C (lit.)
끓는 점
167.16°C (rough estimate)
알파
[α]D20 -0.5~+0.5° (c=5, H2O)
밀도
1.609
증기 밀도
4.6 (vs air)
증기압
<0.1 mm Hg ( 20 °C)
굴절률
1.3920 (estimate)
인화점
203 °C
저장 조건
2-8°C
용해도
methanol: 0.1 g/mL, clear, colorless
물리적 상태
neat
산도 계수 (pKa)
3.4(at 25℃)
수소이온지수(pH)
2.3 (10g/l, H2O, 20℃)
optical activity
[α]/D 0.10 to +0.10°
수용성
558 g/L (20 ºC)
Merck
14,5707
BRN
1723539
CAS 데이터베이스
6915-15-7(CAS DataBase Reference)
NIST
Hydroxybutanedioic acid(6915-15-7)
EPA
Malic acid (6915-15-7)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn,Xi
위험 카페고리 넘버 22-37/38-41-36/37/38-42/43-34
안전지침서 26-39-37/39-36-36/39
WGK 독일 1
RTECS 번호 ON7175000
자연 발화 온도 644 °F
TSCA Yes
HS 번호 29181980
유해 물질 데이터 6915-15-7(Hazardous Substances Data)
독성 LD50 orally in Rabbit: > 3200 mg/kg
기존화학 물질 KE-20414
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
H318 눈에 심한 손상을 일으킴 심한 눈 손상 또는 자극성 물질 구분 1 위험 P280, P305+P351+P338, P310
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
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.
P337+P313 눈에 대한 자극이 지속되면 의학적인 조치· 조언를 구하시오.
P405 밀봉하여 저장하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

말레익산 MSDS


DL-Hydroxybutanedioic acid

말레익산 C화학적 특성, 용도, 생산

개요

사과산은 사과등 천연과일 및 야채에 다량 함유되어 있으며, 사람의 탄수화물 신진대사에 필요한 산미제입니다. 같은 산미제인 구연산에 비해 산도가 강하며 사과산을 사용할 경우 약 20%가 절약될 뿐만 아니라 우아하고 세련된 고급 산미를 나타내고 산미(酸味) 지속이 훨씬 길어 사람의 입맛을 한층 즐겁게 하여 줍니다.

용도

특히 구미에서는 Aspartame등 인조당을 사용하는 건강식품(Diet Food/Drinks)제조에는 필수불가결하게 사용됩니다. 또한사과산은 융점이 낮아 캔디(Candy)등 딱딱한 식품의 산미제로도 많이 쓰입니다.

화학적 성질

White to nearly white crystals or crystal powder

화학적 성질

White or nearly white, crystalline powder or granules having a slight odor and a strongly acidic taste. It is hygroscopic. The synthetic material produced commercially in Europe and the USA is a racemic mixture, whereas the naturally occurring material found in apples and many other fruits and plants is levorotatory.

용도

Malic acid, HOOCCH(OH).CH2COOH, also known as hydroxysuccinic acid, is a colorless solid. It is soluble in water and alcohol. Malic acid exists in two optically active forms and a racemic mixture. It is used in medicine and found in apples and other fruits.
The naturally occuring isomer is the L-form which has been found in apples and many other fruits and plants. Selective α-amino protecting reagent for amino acid derivatives. Versatile synthon for the preparation of chiral compounds including κ-opioid rece

용도

malic acid is the third smallest alpha hydroxy acid in terms of molecular size. Although it is used in numerous cosmetic products, particularly those indicating a “fruit acid” content and generally designed for anti-aging, unlike glycolic and lactic acids, its skin benefits have not been extensively studied. Some formulators consider it difficult to work with, particularly when compared to other AHAs, and it can be somewhat irritating. It is rarely used as the only AHA in a product. It is found naturally occurring in apples.

용도

Malic Acid is an acidulant that is the predominant acid in apples. it exists as white crystalline powder or granules and is considered hygroscopic. as compared to citric acid, it is slightly less soluble but is still readily soluble in water with a solubility of 132 g/100 ml at 20°c. it has a stronger apparent acid taste and has a longer taste retention than citric acid which peaks faster but does not mask the aftertaste as effectively. a quantity of 0.362–0.408 kg of malic acid is equivalent to 0.453 kg of citric acid and to 0.272–0.317 kg of fumaric acid in tartness. at temperatures above 150°c it begins to lose water very slowly to yield fumaric acid. it is used in soft drinks, dry-mix beverages, puddings, jellies, and fruit filling. it is used in hard can- dies because it has a lower melting point (129°c) than citric acid which improves the ease of incorporation.

정의

ChEBI: A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.

생산 방법

Malic acid is manufactured by hydrating maleic and fumaric acids in the presence of suitable catalysts. The malic acid formed is then separated from the equilibrium product mixture.

정의

A colorless crystalline carboxylic acid that is found in unripe fruits. It tastes of apples and is used in food flavorings.

생명 공학 생산

DL-malic acid as well as L-malic acid can be used in beverage, food, and animal nutrition. DL-malic acid is mainly derived from chemical synthesis, whereas L-malic acid is produced biotechnologically by enzymatic or fermentative processes.
Fumaric acid can be converted to L-malic acid using fumarases. Different microorganisms (e.g. Brevibacterium flavum, Brevibacterum ammoniagenes, and Corynebacterium species) are able to form naturally high amounts of fumarase intracellularly. For example, B. flavum has been immobilized in j-carrageenan and polyethyleneimine for whole-cell biocatalysis. A fumarase activity of 2.16 mmol.ml(gel)-1.h -1 at 55 C has been reported. This process has been used to produce 30 metric tons of L-malic acid per month in a continuous process with a 1,000 L column fed at a flow rate of 450 L.h-1 of 1 M sodium fumarate solution. Genetic engineering has been used to improve productivity, by which S. cerevisiae is modified to overexpress fumarase. With this method, a conversion rate of 65 mmol.g-1.h -1 has been observed.
Another possibility is the cultivation of an L-malic acid forming microorganism (e.g. Aspergillus flavus or Schizophyllum commune). The best results have been achieved by cultivation of A. flavus on glucose.Afinal product concentration of 113 g.L-1 with a yield of 1.26 mol of malic acid per mole of glucose and a productivity of 0.59 g.L-1.h-1 has been measured. Moreover, new biotechnological routes have been described using metabolically engineered S. cereviciae. In batch cultivations, concentrations up to 59 g.L-1 with a yield of 0.42 mol of malic acid per mole of glucose and a productivity of 0.19 g.L-1.h-1 have been observed.

Pharmaceutical Applications

Malic acid is used in pharmaceutical formulations as a generalpurpose acidulant. It possesses a slight apple flavor and is used as a flavoring agent to mask bitter tastes and provide tartness. Malic acid is also used as an alternative to citric acid in effervescent powders, mouthwashes, and tooth-cleaning tablets.
In addition, malic acid has chelating and antioxidant properties. It may be used with butylated hydroxytoluene as a synergist in order to retard oxidation in vegetable oils. In food products it may be used in concentrations up to 420 ppm.
Therapeutically, malic acid has been used topically in combination with benzoic acid and salicylic acid to treat burns, ulcers, and wounds. It has also been used orally and parenterally, either intravenously or intramuscularly, in the treatment of liver disorders, and as a sialagogue.

Mechanism of action

Malic acid is absorbed from the gastrointestinal tract from whence it is transported via the portal circulation to the liver. There are a few enzymes that metabolize malic acid. Malic enzyme catalyzes the oxidative decarboxylation of L-malate to pyruvate with concomitant reduction of the cofactor NAD+ (oxidized form of nicotinamide adenine dinucleotide) or NADP+ (oxidized form of nicotinamide adenine dinucleotide phosphate). These reactions require the divalent cations magnesium or manganese. Three isoforms of malic enzyme have been identified in mammals: a cytosolic NADP+-dependent malic enzyme, a mitochondrial NADP+- dependent malic enzyme and a mitochondrial NAD(P)+-dependent malic enzyme. The latter can use either NAD+ or NADP+ as the cofactor but prefers NAD+. Pyruvate formed from malate can itself be metabolized in a number of ways, including metabolism via a number of metabolic steps to glucose. Malate can also be metabolized to oxaloacetate via the citric acid cycle. The mitochondrial malic enzyme, particularly in brain cells may play a key role in the pyruvate recycling pathway, which utilizes dicarboxylic acids and substrates, such as glutamine, to provide pyruvate to maintain the citric acid cycle activity when glucose and lactate are low.

Safety Profile

A poison by intraperitoneal route. Moderately toxic by ingestion. A skin and severe eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Safety

Malic acid is used in oral, topical, and parenteral pharmaceutical formulations in addition to food products, and is generally regarded as a relatively nontoxic and nonirritant material. However, concentrated solutions may be irritant.
LD50 (rat, oral): 1.6 g/kg(3)
LD50 (rat, IP): 0.1 g/kg

저장

Malic acid is stable at temperatures up to 150°C. At temperatures above 150°C it begins to lose water very slowly to yield fumaric acid; complete decomposition occurs at about 180°C to give fumaric acid and maleic anhydride.
Malic acid is readily degraded by many aerobic and anaerobic microorganisms. Conditions of high humidity and elevated temperatures should be avoided to prevent caking.
The effects of grinding and humidity on malic acid have also been investigated.
The bulk material should be stored in a well-closed container, in a cool, dry place.

Purification Methods

Crystallise the acid from acetone, then from acetone/CCl4, or from ethyl acetate by adding pet ether (b 60-70o). Dry it at 35o under 1mm pressure to avoid formation of the anhydride. [Beilstein 3 IV 1124.]

비 호환성

Malic acid can react with oxidizing materials. Aqueous solutions are mildly corrosive to carbon steels.

Regulatory Status

GRAS listed. Both the racemic mixture and the levorotatory isomer are accepted as food additives in Europe. The DL and L forms are included in the FDA Inactive Ingredients Database (oral preparations). Included in nonparenteral and parenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Nonmedicinal Ingredients.

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