23313-12-4

Basic information

• Product Name: L-ASCORBIC ACID 2-MONOPHOSPHATE TRI-CYCLOHEXYLAMMONIUM SALT
• Synonyms: Vitamin C phosphate;l-ascorbic acid 2-monophosphate tris-cyclohexylammonium salt;ascorbate-2-phosphate;Ascorbyl monophosphate;Ascorbyl-2-monophosphate;Ascorbyl-2-phosphate;L-Ascorbic acid, 2-(dihydrogen phosphate);MIJPAVRNWPDMOR-ZAFYKAAXSA-N
• CAS NO: 23313-12-4
• Molecular Formula: C₆H₉O₉P
• Molecular Weight: 553.64
• EINECS: 1312995-182-4
• Mol File: 23313-12-4.mol

Chemical Properties

• Boiling Point: 561.26 °C at 760 mmHg
• Flash Point: 293.239 °C
• Appearance: /
• Density: 2.013 g/cm³
• PKA: 1.38±0.10(Predicted)
• CAS DataBase Reference: L-ASCORBIC ACID 2-MONOPHOSPHATE TRI-CYCLOHEXYLAMMONIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: L-ASCORBIC ACID 2-MONOPHOSPHATE TRI-CYCLOHEXYLAMMONIUM SALT(23313-12-4)
• EPA Substance Registry System: L-ASCORBIC ACID 2-MONOPHOSPHATE TRI-CYCLOHEXYLAMMONIUM SALT(23313-12-4)

Safety Data

• Hazardous Substances Data: 23313-12-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-ASCORBIC ACID 2-MONOPHOSPHATE TRI-CYCLOHEXYLAMMONIUM SALT is used as a therapeutic agent for its potential applications in the treatment of certain diseases and conditions. Its anti-inflammatory and immunomodulatory effects contribute to its efficacy in managing various health issues.
Used in Food and Beverage Industry:
L-ASCORBIC ACID 2-MONOPHOSPHATE TRI-CYCLOHEXYLAMMONIUM SALT is used as a preservative and nutrient enhancer in food and beverage products. Its antioxidant properties help maintain the freshness and quality of the products while providing essential nutrients.
Used in Cosmetics Industry:
L-ASCORBIC ACID 2-MONOPHOSPHATE TRI-CYCLOHEXYLAMMONIUM SALT is used as an active ingredient in skincare products for its antioxidant properties and its ability to promote collagen synthesis. This helps improve skin health, reduce signs of aging, and provide a youthful appearance.
The tri-cyclohexylammonium salt form of L-ascorbic acid 2-monophosphate enhances its solubility and bioavailability, making it easier to incorporate into various products and formulations across these industries.

Upstream product

• 15042-01-0 O-5,6-isopropylidene-L-(+)ascorbic acid 
• 50-81-7 ascorbic acid 

Downstream Products

• 50-81-7 ascorbic acid 

Relevant articles and documents

Production method of L-ascorbic acid-2-phosphate

The invention discloses a production method of a feed additive L-ascorbic acid-2-phosphate. The method comprises the following steps: taking vitamin C as a raw material, carrying out alkalization by using calcium hydroxide turbid liquid under the protection of nitrogen, carrying out esterification by using sodium trimetaphosphate, carrying out curing in a low-oxygen storeroom, and carrying out hot air drying by using nitrogen so as to obtain the L-ascorbic acid-2-phosphate. The method comprises the four steps of an alkalization process, an esterification process, a curing process and a drying process. According to the L-ascorbic acid-2-phosphate product obtained through production with the method disclosed by the invention, the problems usually existing and difficult to solve in the production process of the traditional production technology of the L-ascorbic acid-2-phosphate are solved, and the problems are specifically described as follows: (1) the content is relatively low (the content of national standard requirement is greater than or equal to 35%); (2) the uniformity of a finished product is poor, and the particle size is non-uniform; (3) the finished product has the problem of color difference, and the appearances and colors are also different.

AN IMPROVED SYNTHESIS OF L-ASCORBATE 2-POLYPHOSPHATE

L-Ascorbate (0) reacted rapidly with sodium trimetaphosphate (STMP) at 20-25 deg C and constant pH 9.5-10.0 in the presence of calcium ion.Barium and strontium ions also catalyzed the phosphorylation reaction, but not magnesium ion.The optimum reaction mixture was initially 1.4 M L-ascorbate, 1.8 M STMP, 1.7 M calcium hydroxide, and 0.4 M calcium chloride.Over a 20-min reaction period, pH was maintained by adding approximately 0.1 g calcium hydroxide in a 20percent aqueous slurry.The initial and final Ca/P ratios were ca. 0.36 and 0.42, respectively.The reaction products were 98.8percent 2-phosphorylated L-ascorbate, 1.2percent unreacted 0, and a trace of 4,5-ene, probably formed through 5,6-phosphorylated L-ascorbate 2-polyphosphate.High-performance liquid chromatography with UV detection and preparative anion-exchange chromatography showed the presence of eight 2-phosphorylated derivatives of 0 and two of the 4,5-ene skeleton.Rapid 2-phosphorylation prevented accumulation of the 4,5-elimination reaction, and three 5,6-cyclophosphoesters of 0 were found in the reaction products.A Ca/Na (3/1) salt of L-ascorbate 2-polyphosphate was isolated in 88percent yield as a white, odorless powder containing 33percent of L-ascorbate equivalents.Crystalline cyclohexylammonium salts of L-ascorbate 2-mono, di, and triphosphates were prepared.

Enzymatic Production of Ascorbic Acid-2-phosphate

Microorganisms that produce ascorbic acid-2-phosphate (AsA2P) from ascorbic acid (AsA) and ATP were screened from our culture collection.Of 715 strains, three microorganisms, Pseudomonas azotocolligans KY4661, P. paucimobilis KY4084, and an unidentified bacterium KY3132 were selected as AsA2P-producers.When using 50mg (wet weight) of P. azotocolligans cells per ml as the enzyme source, 3.7mM AsA2P were produced for 23 hr, from 30mM AsA and 40mM ATP.From analytical data of the purified product from the reaction mixture, these microorganisms phosphorylated AsA at the C-2 position specifically.

X-Ray Analysis of L-Ascorbic Acid 2-O-Phosphate

L-Ascorbic acid 2-O-phosphate,synthesized from 5,6-O-isopropylidene L-ascorbic acid by reaction with phosphoryl chloride in alkaline water-pyridine solution, crystallized as colorless plates of the dipiperazinium salt trihydrate, C6H9O9P*2C4H10N2*3H2O.Its molecular structure was determined by X-ray analisys.Keywords--Piperazinium L-ascorbic acid 2-O-phosphate; Magnesium L-ascorbic acid 2-O-phosphate; X-ray analysis; structure determination; CMR