아스코르브산

아스코르브산
아스코르브산 구조식 이미지
카스 번호:
36431-82-0
한글명:
아스코르브산
동의어(한글):
아스코르브산
상품명:
Ascoric Acid
동의어(영문):
Ascoric Acid;Ascoric Acid USP/EP/BP;1-(4-phenethylpiperazin-1-yl)-2-(1-phenylcyclohexyl)ethanoneascorbate;Piperazine, 1-((1-phenylcyclohexyl)acetyl)-4-(2-phenylethyl)-, coMpd. with L-ascorbic acid
CBNumber:
CB32130241
분자식:
C32H42N2O7
포뮬러 무게:
566.7
MOL 파일:
36431-82-0.mol

아스코르브산 속성

산도 계수 (pKa)
4.1(at 24℃)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
그림문자(GHS): GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H304 삼켜서 기도로 유입되면 치명적일 수 있음 흡인 유해성물질 구분 1 위험 GHS hazard pictograms
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H336 졸음 또는 현기증을 일으킬 수 있음 특정표적장기 독성 물질(1회 노출);마취작용 구분 3 경고 P261, P271, P304+P340, P312,P403+P233, P405, P501
H411 장기적 영향에 의해 수생생물에 유독함 수생 환경유해성 물질 - 만성 구분 2
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P271 옥외 또는 환기가 잘 되는 곳에서만 취급하시오.
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.
P312 불편함을 느끼면 의료기관(의사)의 진찰을 받으시오.
P403+P233 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 저장하시오.
P405 밀봉하여 저장하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

아스코르브산 C화학적 특성, 용도, 생산

개요

Ascorbic acid is a naturally occurring organic compound with antioxidant properties. It is a white solid, but impure samples can appear yellowish. It dissolves well in water to give mildly acidic solutions. Ascorbic acid is one form ("vitamer") of vitamin C. It was originally called L-hexuronic acid, but when it was found to have vitamin C activity in animals ("vitamin C" being defined as a vitamin activity, not then a specific substance), the suggestion was made to rename L-hexuronic acid. The new name for L-hexuronic acid is derived from a- (meaning "no") and scorbutus (scurvy), the disease caused by a deficiency of vitamin C. Because it is derived from glucose, many animals are able to produce it, but humans require it as part of their nutrition. Other vertebrates lacking the ability to produce ascorbic acid include other primates, guinea pigs, teleost fishes, bats,and birds, all of which require it as a dietary micronutrient (that is, a vitamin).

화학적 성질

Ascorbic acid is present in nutritionally useful amounts in many edible plants, especially in rapidly growing leafy vegetables, fruits, tomatoes and potatoes. Foods of animal origin as usually consumed are generally poor sources of the vitamin. Of the stereoisomers (L-ascorbic acid, D-ascorbic acid, L-isoascorbic acid and D-isoascorbic acid or erythorbic acid), only L-ascorbic acid has significant vitamin C activity. The vitamin C activity of ascorbyl palmitate is approximately equal to that of L-ascorbic acid. Ascorbic acid has a pleasant, sharp, acidic taste without any odor. It is extensively used as antioxidant, meat-curing aid, nutrient and dietary supplement. For a detailed description, see Burdock (1997).

출처

Reported found in rose hip, black currants, the juice of citrus fruits and the ripe fruit of Capsicum annuum L.

역사

From the middle of the 18th century, it was noted that lemon juice could prevent sailors from getting scurvy. At first, it was supposed that the acid properties were responsible for this benefit; however, it soon became clear that other dietary acids, such as vinegar, had no such benefits. In 1907, two Norwegian physicians reported an essential disease-preventing compound in foods that was distinct from the one that prevented beriberi. These physicians were investigating dietary deficiency diseases using the new animal model of guinea pigs, which are susceptible to scurvy. The newly discovered food-factor was eventually called vitamin C.
From 1928 to 1932, the Hungarian research team led by Albert Szent-Gy?rgyi, as well as that of the American researcher Charles Glen King, identified the antiscorbutic factor as a particular single chemical substance. At the Mayo clinic, Szent-Gy?rgyi had isolated the chemical hexuronic acid from animal adrenal glands. He suspected it to be the antiscorbutic factor, but could not prove it without a biological assay. This assay was finally conducted at the University of Pittsburgh in the laboratory of King, which had been working on the problem for years, using guinea pigs. In late 1931, King's lab obtained adrenal hexuronic acid indirectly from Szent-Gy?rgyi and using their animal model, proved that it is vitamin C, by early 1932.

용도

Vitamin (antiscorbutic); acidifier (urinary).

제조 방법

Ascorbic acid is prepared industrially from glucose in a method based on the historical Reichstein process. In the first of a five-step process, glucose is catalytically hydrogenated to sorbitol, which is then oxidized by the microorganism Acetobacter suboxydans to sorbose. Only one of the six hydroxy groups is oxidized by this enzymatic reaction. From this point, two routes are available. Treatment of the product with acetone in the presence of an acid catalyst converts four of the remaining hydroxyl groups to acetals. The unprotected hydroxyl group is oxidized to the carboxylic acid by reaction with the catalytic oxidant TEMPO (regenerated by sodium hypochlorite — bleaching solution). (Historically, industrial preparation via the Reichstein process used potassium permanganate.) Acid-catalyzed hydrolysis of this product performs the dual function of removing the two acetal groups and ring-closing lactonization. This step yields ascorbic acid. Each of the five steps has a yield larger than 90 %.

화학 반응

Ascorbic acid resembles the sugar from which it is derived, being a ring with many oxygen-containing functional groups. The molecule exists in equilibrium with two ketone tautomers, which are less stable than the enol form . In solutions, these forms of ascorbic acid rapidly interconvert.
Nucleophilic attack of ascorbic enol on proton to give 1,3-diketone.

Biosynthesis

Ascorbic acid is found in plants and animals where it is produced from glucose. Animals must either produce it or digest it, otherwise a lack of vitamin C may cause scurvy which may eventually lead to death. Reptiles and older orders of birds make ascorbic acid in their kidneys. Recent orders of birds and most mammals make ascorbic acid in their liver where the enzyme L-gulono lactone oxidase is required to convert glucose to ascorbic acid. Humans, some other primates, and guinea pigs are not able to make L-gulono lactone oxidase because of a genetic mutation and are therefore unable to make ascorbic acid. Synthesis and signalling properties are still under investigation.

Mechanism of action

As a mild reducing agent, ascorbic acid degrades upon exposure to air, converting the oxygen to water. The redox reaction is accelerated by the presence of metal ions and light. It can be oxidized by one electron to a radical state or doubly oxidized to the stable form called dehydroascorbic acid.
Ascorbate usually acts as an antioxidant. It typically reacts with oxidants of the reactive oxygen species, such as the hydroxyl radical formed from hydrogen peroxide. Such radicals are damaging to animals and plants at the molecular level due to their possible interaction with nucleic acids, proteins, and lipids. Sometimes these radicals initiate chain reactions. Ascorbate can terminate these chain radical reactions by electron transfer. Ascorbic acid is special because it can transfer a single electron, owing to the stability of its own radical ion called "semidehydroascorbate", dehydroascorbate. The net reaction is :
RO? + C6H7O6- → ROH + C6H6O6?-
The oxidized forms of ascorbate are relatively unreactive, and do not cause cellular damage.
However, being a good electron donor, excess ascorbate in the presence of free metal ions can not only promote but also initiate free radical reactions, thus making it a potentially dangerous pro-oxidative compound in certain metabolic contexts.
Acidity
Ascorbic acid, a reductone, behaves as a vinylogous carboxylic acid wherein the electrons in the double bond, hydroxyl group lone pair, and the carbonyl double bond form a conjugated system. Because the two major resonance structures stabilize the deprotonated conjugate base of ascorbic acid, the hydroxyl group in ascorbic acid is much more acidic than typical hydroxyl groups. In other words, ascorbic acid can be considered an enol in which the deprotonated form is a stabilized enolate.

아스코르브산 준비 용품 및 원자재

원자재

준비 용품


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