L(+)-Ascorbic acid

Base Information

• Chemical Name: L(+)-Ascorbic acid
• CAS No.: 50-81-7
• Molecular Formula: C6H8O6
• Molecular Weight: 176.126
• Hs Code.: 29362700
• Mol file: 50-81-7.mol

Synonyms:L(+)-Ascorbic acid;L-Ascorbic acid（C);(R)-5-((S)-1,2-Dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one;L-Ascorbic acid;L-Threoascorbic acid,Antiscorbutic factor,Vitamin C;L-Ascorbic Acid;

Chemical Property of L(+)-Ascorbic acid

Chemical Property:

• Appearance/Colour: white crystals
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 190-194 °C (dec.)
• Refractive Index: 21 ° (C=10, H2O)
• Boiling Point: 415.8 °C at 760 mmHg
• PKA: 4.04, 11.7(at 25℃)
• Flash Point: 180.4 °C
• PSA: 107.22000
• Density: 1.954 g/cm³
• LogP: -1.40740
• Storage Temp.: 0-6°C
• Solubility.: H2O: 50 mg/mL at 20 °C, clear, nearly colo
• Water Solubility.: 333 g/L (20 ºC)

Purity/Quality:

99.5% ^*data from raw suppliers

Ascorbic Acid USP ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Role and Importance: Ascorbic acid, also known as vitamin C, serves various essential functions in the human body. It acts as an antioxidant, a cofactor for numerous enzymatic reactions, a coenzyme, a flour treatment agent, a food antioxidant, a plant metabolite, a skin-lightening agent, and a food color retention agent.
• Discovery and History: L-ascorbic acid was first described and isolated in 1928 by Hungarian biochemist Albert Szent-Gy枚rgyi, who won the Nobel Prize in 1937 for his work. Its name "ascorbic acid" is derived from "scurvy" (scorbutus), as its deficiency was initially associated with the development of scurvy.
• Chemical Structure and Properties: Ascorbic acid is an organic compound belonging to the group of unsaturated polyhydroxy alcohols. It is a water-soluble ketolactone with a five-membered carbon ring. It has strong reducing properties due to double bonds at the C2 and C3 carbons and four hydroxyl groups. Ascorbic acid serves as a hydrogen or electron donor, making it a cofactor in many enzymatic reactions.
• Dietary Requirement and Sources: While most mammals can produce ascorbic acid from glucose, humans lack the necessary enzyme and must obtain it from their diet. The daily requirement for ascorbic acid intake varies, with women needing around 75 mg and men around 90 mg. While citrus fruits are commonly associated with ascorbic acid, other fruits, vegetables, and meats also serve as dietary sources.
• Antioxidant Properties: Ascorbic acid is a key low-molecular-weight antioxidant that regulates levels of reactive oxygen species (ROS) and enhances the effectiveness of other antioxidants. It plays a role in ROS regulation at their formation stage and donates a single reducing equivalent. It stimulates the activity of antioxidant enzymes like superoxide dismutase (SOD) and is crucial for collagen synthesis.

Technology Process of L(+)-Ascorbic acid

There total 75 articles about L(+)-Ascorbic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

dikegulac (18467-77-1) → ascorbic acid (50-81-7,98966-42-8)

Guidance literature:

With hydrogenchloride; In toluene; at 70 ℃; for 6h;

DOI:10.1023/A:1010400616941

Reference yield: 83.0%

Methyl 2-keto-3,5:4,6-di-O-ethylidene-L-galactonate → ascorbic acid (50-81-7,98966-42-8)

Guidance literature:

With hydrogenchloride; In ethanol; dichloromethane; at 60 ℃; for 10h;

DOI:10.1021/jo00077a062

Reference yield: 83.0%

methyl 2-keto-3,5:4,6-di-O-ethylidene galactonate (144447-58-5) → ascorbic acid (50-81-7,98966-42-8)

Guidance literature:

With hydrogenchloride; ethanol; In dichloromethane; at 60 ℃;

DOI:10.1016/S0040-4039(00)61188-7

upstream raw materials:

L-xylosone

2-keto-L-gulonic acid

L-lyxo-[2]hexulosonic acid

(3R,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxo-hexanoic acid methyl ester

Downstream raw materials:

2,3-di-O-methyl-L-ascorbic acid

4-Nitro-N-phenylhydroxylamine

2-Hydroxylamino-5-nitro-benzoesaeure

4-(hydroxyamino)benzoic acid

Refernces

• 1、 Hayashi,Namiki,Tsuji. "Formation mechanism of the free radical product and its precursor by the reaction of dehydro-L-ascorbic acid with amino acid". . p. 1955 - 1960. Retrieved 1983.
• 2、 Wang, Kan,Jiang, Ling,Zhang, Fen,Wei, Yuanqing,Wang, Kang,Wang, Huaisheng,Qi, Zhengjian,Liu, Songqin. "Strategy for in Situ Imaging of Cellular Alkaline Phosphatase Activity Using Gold Nanoflower Probe and Localized Surface Plasmon Resonance Technique". . p. 14056 - 14062. Retrieved 2018.
• 3、 Fan, Yongchao,Lv, Mengmeng,Xue, Yuan,Li, Jing,Wang, Erkang. "In Situ Fluorogenic Reaction Generated via Ascorbic Acid for the Construction of Universal Sensing Platform". . p. 6873 - 6880. Retrieved 2021.
• 4、 Dereven'kov, Ilia A.,Hannibal, Luciana,Dürr, Maximilian,Salnikov, Denis S.,Bui Thi, Thu Thuy,Makarov, Sergei V.,Koifman, Oscar I.,Ivanovi?-Burmazovi?, Ivana. "Redox turnover of organometallic B12 cofactors recycles vitamin C: Sulfur assisted reduction of dehydroascorbic acid by cob(II)alamin". . p. 53 - 59. Retrieved 2017.
• 5、 Zhao, Dan,Li, Juan,Peng, Chuanyun,Zhu, Shuyun,Sun, Jian,Yang, Xiurong. "Fluorescence Immunoassay Based on the Alkaline Phosphatase Triggered in Situ Fluorogenic Reaction of o-Phenylenediamine and Ascorbic Acid". . . Retrieved 2019.
• 6、 Andrews et al.. "-". . p. 740. Retrieved 1979.
• 7、 Wang, Zongwen,Chen, Qian,Zhong, Yingying,Yu, Xinhui,Wu, Yongning,Fu, FengFu. "A multicolor immunosensor for sensitive visual detection of breast cancer biomarker based on sensitive nadh-ascorbic-acid-mediated growth of gold nanobipyramids". . p. 1534 - 1540. Retrieved 2020.
• 8、 Jiang, Xiaoqian,Wang, Xiaoyu,Lin, Anqi,Wei, Hui. "In Situ Exsolution of Noble-Metal Nanoparticles on Perovskites as Enhanced Peroxidase Mimics for Bioanalysis". . p. 5954 - 5962. Retrieved 2021.
• 9、 Csiba, M.,Cleophax, J.,Petit, S.,Gero, S. D.. "An Expedient and Practical Three-Step Synthesis of Vitamin C from a Byproduct of the Sugar Industry: The L-Galactono-1,4-lactone Pathway". . p. 7281 - 7282. Retrieved 1993.
• 10、 Chen, Zi-Jian,Wu, Hui-Ling,Shen, Yu-Dong,Wang, Hong,Zhang, Yi-Feng,Hammock, Bruce,Li, Zhen-Feng,Luo, Lin,Lei, Hong-Tao,Xu, Zhen-Lin. "Phosphate-triggered ratiometric fluoroimmunoassay based on nanobody-alkaline phosphatase fusion for sensitive detection of 1-naphthol for the exposure assessment of pesticide carbaryl". . . Retrieved 2021/10/12.