ChemicalBook > CAS DataBase List > L(+)-Ascorbic acid

L(+)-Ascorbic acid

Product Name
L(+)-Ascorbic acid
CAS No.
50-81-7
Chemical Name
L(+)-Ascorbic acid
Synonyms
100M;Celin;Cevex;Cewin;Cipca;Vicin;Cebid;Cecon;Hicee;IDO-C
CBNumber
CB7853704
Molecular Formula
C6H8O6
Formula Weight
176.12
MOL File
50-81-7.mol
More
Less

L(+)-Ascorbic acid Property

Melting point:
190-194 °C (dec.)
alpha 
20.5 º (c=10,H2O)
Boiling point:
227.71°C (rough estimate)
Density 
1,65 g/cm3
FEMA 
2109 | ASCORBIC ACID
refractive index 
21 ° (C=10, H2O)
storage temp. 
0-6°C
solubility 
H2O: 50 mg/mL at 20 °C, clear, nearly colorless
form 
powder
pka
4.04, 11.7(at 25℃)
color 
white to slightly yellow
PH
1.0 - 2.5 (25℃, 176g/L in water)
PH Range
1 - 2.5
Odor
Odorless
optical activity
[α]25/D 19.0 to 23.0°, c = 10% in H2O
Water Solubility 
333 g/L (20 ºC)
Merck 
14,830
BRN 
84272
Stability:
Stable. May be weakly light or air sensitive. Incompatible with oxidizing agents, alkalies, iron, copper.
InChIKey
CIWBSHSKHKDKBQ-JLAZNSOCSA-N
CAS DataBase Reference
50-81-7(CAS DataBase Reference)
NIST Chemistry Reference
L-Ascorbic acid(50-81-7)
EPA Substance Registry System
Ascorbic acid (50-81-7)
More
Less

Safety

Hazard Codes 
Xn
Risk Statements 
20/21/22-36/37/38
Safety Statements 
24/25-36-26
RIDADR 
UN 1648 3 / PGII
WGK Germany 
1
RTECS 
CI7650000
TSCA 
Yes
HS Code 
29362700
Hazardous Substances Data
50-81-7(Hazardous Substances Data)
Toxicity
LD50 oral in rat: 11900mg/kg
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H226Flammable liquid and vapour

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P370+P378In case of fire: Use … for extinction.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
255564
Product name
L-Ascorbic acid
Purity
ACS reagent, ≥99%
Packaging
5g
Price
$42.2
Updated
2020/08/18
Sigma-Aldrich
Product number
1043003
Product name
Ascorbic acid
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
1g
Price
$371
Updated
2020/08/18
TCI Chemical
Product number
A0537
Product name
L-Ascorbic Acid
Purity
>99.0%(T)
Packaging
25g
Price
$15
Updated
2020/06/24
TCI Chemical
Product number
A0537
Product name
L-Ascorbic Acid
Purity
>99.0%(T)
Packaging
500g
Price
$38
Updated
2020/06/24
Alfa Aesar
Product number
011188
Product name
L-(+)-Ascorbic acid, 98+%
Packaging
100g
Price
$25.6
Updated
2020/06/24
More
Less

L(+)-Ascorbic acid Chemical Properties,Usage,Production

Description

Ascorbic acid, a water-soluble dietary supplement, is consumed by humans more than any other supplement. The name ascorbic means antiscurvy and denotes the ability of ascorbic to combat this disease. Vitamin C is the l-enantiomer of ascorbic acid. Ascorbic acid deficiency in humans results in the body’s inability to synthesize collagen, which is the most abundant protein in vertebrates.

Chemical Properties

White crystals (plates or needles). Soluble in water; slightly soluble in alcohol; insoluble in ether, chloroform, benzene, petroleum ether, oils and fats. Stable to air when dry. One international unit is equivalent to 0.05 milligram of l-ascorbic acid.

Chemical Properties

Ascorbic acid occurs as a white to light-yellow-colored, nonhygroscopic, odorless, crystalline powder or colorless crystals with a sharp, acidic taste. It gradually darkens in color upon exposure to light.

Originator

Ascorbic aci,Natur Product,France

Uses

The starting point for synthesis of vitamin C is the selective of oxidation of the sugar compound D-sorbit to L-sorbose using Acetobacter suboxidans bacteria. L-sorbose is then converted to L-ascorbic acid, better known as vitamin C.

Uses

Sodium, potassium, and calcium salts of ascorbic acids are called ascorbates and are used as food preservatives. To make ascorbic acid fat-soluble, it can be esterified. Esters of ascorbic acid and acids, such as palmitic acid to form ascorbyl palmitate and stearic acid to form ascorbic stearate, are used as antioxidants in food, pharmaceuticals, and cosmetics. Ascorbic acid is also essential in the metabolism of some amino acids. It helps protect cells from free radical damage, helps iron absorption, and is essential for many metabolic processes.

Uses

vitamin C is a well-known anti-oxidant. Its effect on free-radical formation when topically applied to the skin by means of a cream has not been clearly established. The effectiveness of topical applications has been questioned due to vitamin C’s instability (it reacts with water and degrades). Some forms are said to have better stability in water systems. Synthetic analogues such as magnesium ascorbyl phosphate are among those considered more effective, as they tend to be more stable. When evaluating its ability to fight free-radical damage in light of its synergistic effect with vitamin e, vitamin C shines. As vitamin e reacts with a free radical, it, in turn, is damaged by the free radical it is fighting. Vitamin C comes in to repair the free-radical damage in vitamin e, allowing e to continue with its free-radical scavenging duties. Past research has indicated that high concentrations of topically applied vitamin C are photoprotective, and apparently the vitamin preparation used in these studies resisted soap and water, washing, or rubbing for three days. More current research has indicated that vitamin C does add protection against uVB damage when combined with uVB sunscreen chemicals. This would lead one to conclude that in combination with conventional sunscreen agents, vitamin C may allow for longer-lasting, broader sun protection. Again, the synergy between vitamins C and e can yield even better results, as apparently a combination of both provides very good protection from uVB damage. However, vitamin C appears to be significantly better than e at protecting against uVA damage. A further conclusion is that the combination of vitamins C, e, and sunscreen offers greater protection than the sum of the protection offered by any of the three ingredients acting alone. Vitamin C also acts as a collagen biosynthesis regulator. It is known to control intercellular colloidal substances such as collagen, and when formulated into the proper vehicles, can have a skin-lightening effect. Vitamin C is said to be able to help the body fortify against infectious conditions by strengthening the immune system. There is some evidence (although debated) that vitamin C can pass through the layers of the skin and promote healing in tissue damaged by burns or injury. It is found, therefore, in burn ointments and creams used for abrasions. Vitamin C is also popular in anti-aging products. Current studies indicate possible anti-inflammatory properties as well.

Uses

antiscorbutic, antiviral

Uses

analgesic, antipyretic

Uses

Physiological antioxidant. Coenzyme for a number of hydroxylation reactions; required for collagen synthesis. Widely distributed in plants and animals. Inadequate intake results in deficiency syndrome s such as scurvy. Used as antimicrobial and antioxidant in foodstuffs.

Definition

ChEBI: The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.

Production Methods

Ascorbic acid is prepared synthetically or extracted from various vegetable sources in which it occurs naturally, such as rose hips, blackcurrants, the juice of citrus fruits, and the ripe fruit of Capsicum annuum L. A common synthetic procedure involves the hydrogenation of D-glucose to D-sorbitol, followed by oxidation using Acetobacter suboxydans to form L-sorbose. A carboxyl group is then added at C1 by air oxidation of the diacetone derivative of Lsorbose and the resulting diacetone-2-keto-L-gulonic acid is converted to L-ascorbic acid by heating with hydrochloric acid.

Production Methods

Ascorbic acid is produced synthetically using the Reichstein process, which has been the standard method of production since the 1930s. The process starts with fermentation followed by chemical synthesis. The first step involves reduction of D-glucose at high temperature into D-sorbitol. D-sorbitol undergoes bacterial fermentation, converting it into L-sorbose. L-sorbose is then reacted with acetone in the presence of concentrated sulfuric acid to produce diacetone-L-sorbose, which is then oxidized with chlorine and sodium hydroxide to produce di-acetone-ketogulonic acid (DAKS). DAKS is then esterified with an acid catalyst and organics to give a gulonic acid methylester. The latter is heated and reacted with alcohol to produce crude ascorbic acid, which is then recrystallized to increase its purity. Since the development of the Reichstein process more than 70 years ago, it has undergone many modifications. In the 1960s, a method developed in China referred to as the two-stage fermentation process used a second fermentation stage of L-sorbose to produce a different intermediate than DAKS called KGA (2-keto-L-gulonic acid), which was then converted into ascorbic acid. The two stage process relies less on hazardous chemicals and requires less energy to convert glucose to ascorbic acid.

Indications

Vitamin C (ascorbic acid) is essential for the maintenance of the ground substance that binds cells together and for the formation and maintenance of collagen.The exact biochemical role it plays in these functions is not known, but it may be related to its ability to act as an oxidation–reduction system.

Manufacturing Process

D-Glucose was reduced to the D-sorbitol with a hydrogen over Ni Raney, then it was turned into the L-sorbose with the acetobacter suboxydans and the hydroxyl groups of L-sorbose were protected with acetone treatment yielded the diaceton-L-sorbose. Subsequent treatment with NaOCl/Raney Ni produced di-O-isopropylidene-2-oxo-L-gulonic acid. Partial hydrolysis with aqueous HCl gave deprotected 2-oxo-L-gulonic acid, which yielded ascorbinic acid by heating with HCl.

brand name

Ascorbin (Marion Merrell Dow).

Therapeutic Function

Vitamin

General Description

Scurvy (from the French word scorbutus) has been recognized as a disease afflicting mankind for thousands of years. Citrus fruits such as oranges, lemons, and limes were later identified as equally effective treatments. Only within the last 100 years has a deficiency in vitamin C been definitively identified as the cause of scurvy. In 1932, Waugh and King isolated crystalline vitamin C from lemon juice and showed it to be the antiscorbutic factor present in each of these treatments.
The structure and chemical formula of vitamin C was identified in 1933 by Hirst et al.Because humans are one of the few animal species that cannot synthesize vitamin C, it has to be available as a dietary component. Dietary sources of ascorbic acid include fruits (especially citrus fruits), vegetables (especially peppers), and potatoes. Although the sources of some commercial products are rose hips and citrus fruits, most ascorbic acid is prepared synthetically.
Vitamin C is now commonly referred to as ascorbic acid because of its acidic character and its effectiveness in the treatment and prevention of scorbutus (scurvy). The acidic character is because of the two enolic hydroxyls; the C3 hydroxyl has a pKa value of 4.1, and the C2 hydroxyl has a pKa of 11.6. All biological activities reside in L-ascorbic acid; therefore, all references to vitamin C, ascorbic acid, ascorbate, and their derivatives refer to this form. The monobasic sodium salt is the usual salt form.

General Description

White to very pale yellow crystalline powder with a pleasant sharp acidic taste. Almost odorless.

Air & Water Reactions

May be sensitive to prolonged exposure to air and light. Sensitive to moisture. Soluble in water. Aqueous solutions are oxidized by air in a reaction that is accelerated by alkalis, iron and copper. The rate depends on the pH and on oxygen concentration. Also subject to degradation under anaerobic conditions.

Reactivity Profile

L(+)-Ascorbic acid is a lactone. Reacts as a relatively strong reducing agent and decolorizes many dyes. Forms stable metal salts. Incompatible with oxidizers, dyes, alkalis, iron and copper. Also incompatible with ferric salts and salts of heavy metals, particularly copper, zinc and manganese .

Fire Hazard

Flash point data for L(+)-Ascorbic acid are not available; however, L(+)-Ascorbic acid is probably combustible.

Pharmaceutical Applications

Ascorbic acid is used as an antioxidant in aqueous pharmaceutical formulations at a concentration of 0.01–0.1% w/v. Ascorbic acid has been used to adjust the pH of solutions for injection, and as an adjunct for oral liquids. It is also widely used in foods as an antioxidant. Ascorbic acid has also proven useful as a stabilizing agent in mixed micelles containing tetrazepam.

Clinical Use

Vitamin C is indicated for the treatment and prevention of known or suspect deficiency. Although scurvy occurs infrequently, it is seen in the elderly, infants, alcoholics, and drug users.Ascorbate can also be used to enhance absorption of dietary nonheme iron or iron supplements. Ascorbic acid (but not the sodium salt) was historically used to acidify the urine as a result of excretion of unchanged ascorbic acid, although this use has fallen into disfavor. Ascorbate also increases iron chelation by deferoxamine, explaining its use in the treatment of iron toxicity.

Clinical Use

Vitamin C is found in fresh fruit and vegetables. It is very water soluble, is readily destroyed by heat, especially in an alkaline medium, and is rapidly oxidized in air. Fruit and vegetables that have been stored in air, cut or bruised, washed, or cooked may have lost much of their vitamin C content. The deficiency disease associated with a lack of ascorbic acid is called scurvy. Early symptoms include malaise and follicular hyperkeratosis. Capillary fragility results in hemorrhages, particularly of the gums. Abnormal bone and tooth development can occur in growing children.The body’s requirement for vitamin C increases during periods of stress, such as pregnancy and lactation.

Side effects

Megavitamin intake of vitamin C may result in diarrhea due to intestinal irritation. Since ascorbic acid is partially metabolized and excreted as oxalate, renal oxalate stones may form in some patients.

Toxicology

L-Ascorbic acid, or vitamin C, is widely present in plants. The structures of ascorbic acid and dehydroascorbic acid are shown in Figure 10.5. Vitamin C is not only an important nutrient but is also used as an antioxidant in various foods. However, it is not soluble in fat and is unstable under basic conditions. Vitamin C reduces cadmium toxicity and excess doses prolong the retention time of an organic mercury compound in a biological system. Overdoses of vitamin C (106 g) induce perspiration, nervous tension, and lowered pulse rate. WHO recommends that daily intake be less than 0.15 mg/kg. Toxicity due to ascorbic acid has not been reported. Although repeated intravenous injections of 80 mg dehydroascorbic acid was reported to be diabetogenic in rats, oral consumption of 1.5 g/day of ascorbic acid for six weeks had no effect on glucose tolerance or glycosuria in 12 normal adult males and produced no change in blood glucose concentrations in 80 diabetics after five days. The same report noted that a 100-mg intravenous dose of dehydroascorbic acid given daily for prolonged periods produced no signs of diabetes. Ascorbic acid is readily oxidized to dehydroascorbic acid, which is reduced by glutathione in blood.

Safety Profile

Moderately toxic by ingestion and intravenous routes. Human systemic effects by intravenous route: blood, changes in tubules (including acute renal failure, acute tubular necrosis). An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Safety

Ascorbic acid is an essential part of the human diet, with 40 mg being the recommended daily dose in the UK and 60 mg in the USA. However, these figures are controversial, with some advocating doses of 150 or 250mg daily. Megadoses of 10 g daily have also been suggested to prevent illness although such large doses are now generally considered to be potentially harmful.
The body can absorb about 500 mg of ascorbic acid daily with any excess immediately excreted by the kidneys. Large doses may cause diarrhea or other gastrointestinal disturbances. Damage to the teeth has also been reported. However, no adverse effects have been reported at the levels employed as an antioxidant in foods, beverages, and pharmaceuticals. The WHO has set an acceptable daily intake of ascorbic acid, potassium ascorbate, and sodium ascorbate, as antioxidants in food, at up to 15 mg/kg bodyweight in addition to that naturally present in food.
LD50 (mouse, IV): 0.52 g/kg
LD50 (mouse, oral): 3.37 g/kg
LD50 (rat, oral): 11.9 g/kg

storage

In powder form, ascorbic acid is relatively stable in air. In the absence of oxygen and other oxidizing agents it is also heat stable. Ascorbic acid is unstable in solution, especially alkaline solution, readily undergoing oxidation on exposure to the air.The oxidation process is accelerated by light and heat and is catalyzed by traces of copper and iron. Ascorbic acid solutions exhibit maximum stability at about pH 5.4. Solutions may be sterilized by filtration.
The bulk material should be stored in a well-closed nonmetallic container, protected from light, in a cool, dry place.

Purification Methods

Crystallise it from MeOH/Et2O/pet ether [Herbert et al. J Chem Soc 1270 1933]. [Beilstein 18/5 V 26.]

Incompatibilities

Incompatible with alkalis, heavy metal ions, especially copper and iron, oxidizing materials, methenamine, phenylephrine hydrochloride, pyrilamine maleate, salicylamide, sodium nitrite, sodium salicylate, theobromine salicylate, and picotamide. Additionally, ascorbic acid has been found to interfere with certain colorimetric assays by reducing the intensity of the color produced.

Regulatory Status

GRAS listed. Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (inhalations, injections, oral capsules, suspensions, tablets, topical preparations, and suppositories). Included in medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

More
Less

L(+)-Ascorbic acid Suppliers

Puripharm Co., Ltd.
Tel
0572-2745768-1;0572-2717806-
Fax
13167223168
Email
sales@puripharm.com;yzm@puripharm.com
Country
China
ProdList
218
Advantage
65
Shanghai Shangyao Xinya Pharmaceutical Co., Ltd.
Tel
021-22309200
Email
lingq@xinyaharm.com
Country
CHINA
ProdList
1
Advantage
58
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
021-20337333-801
Fax
021-50323701
Email
market@aladdin-e.com
Country
China
ProdList
24983
Advantage
65
Shandong Fengtai Biotechnology Co., Ltd.
Tel
0531-82066716-
Fax
0531-82066716
Email
528732991@qq.com
Country
China
ProdList
895
Advantage
58
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24555
Advantage
81
Shanghai changwei industrial development co., LTD
Tel
13262956501
Email
cli@sunwayshanghai.com
Country
China
ProdList
298
Advantage
58
Nanjing Benzjia Chemical Co., Ltd.
Tel
18805263762
Email
NJBENJIA@163.COM
Country
China
ProdList
131
Advantage
58
Hubei Jianwen Biomedical Co., Ltd.
Tel
027-87887055-
Fax
027-87887055
Email
2644074018@qq.com
Country
China
ProdList
1062
Advantage
58
HuBei Bass Electronic Material Co.,Ltd
Tel
0716-2852356-
Fax
0716-2853766
Email
bellarongl@basschemical.com
Country
China
ProdList
41
Advantage
58
Sigma-Aldrich
Tel
021-61415566
Email
orderCN@merckgroup.com;orderCN@merckgroup.com
Country
China
ProdList
48614
Advantage
80
More
Less

View Lastest Price from L(+)-Ascorbic acid manufacturers

WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Vitamin C 50-81-7
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-11-20
Wuhan Bosman Medicine Tech Co.,LTD
Product
L-Ascorbicacid 50-81-7
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20 tons
Release date
2021-02-22
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Vitamin C 50-81-7
Price
US $1.00/g
Min. Order
10g
Purity
99%
Supply Ability
1000kgs
Release date
2020-11-25

50-81-7, L(+)-Ascorbic acidRelated Search:


  • 3-Keto-L-gulofuranolactone
  • 3-Oxo-L-gulofuranolactone
  • 3-oxo-l-gulofuranolactone(enolform)
  • Adenex
  • Allercorb
  • Antiscorbic vitamin
  • antiscorbicvitamin
  • Antiscorbutic vitamin
  • antiscorbuticvitamin
  • Arco-Cee
  • Ascoltin
  • Ascorb
  • Celin
  • Cemagyl
  • Ce-Mi-Lin
  • Cemill
  • Cenetone
  • Cereon
  • Cergona
  • Cescorbat
  • Cetamid
  • Cetane-Caps TC
  • Cetane-Caps TD
  • cetane-capstd
  • Cetebe
  • Cetemican
  • Cevalin
  • Cevatine
  • Cevex
  • Cevi-Bid
  • Cevimin
  • Ce-Vi-Sol
  • Cevital
  • Cevitamic acid
  • cevitamicacid
  • Cevitamin
  • Cevitan
  • Cevitex
  • Cewin
  • Ciamin
  • Cipca
  • Citriscorb
  • C-Level
  • C-Long
  • Colascor
  • component of Chromagen
  • component of Cortalex
  • component of E and C-Level
  • component of Endoglobin Forte
  • component of Ferancee
  • component of Freancee
  • component of Stuartinic
  • component of Tolfrinic
  • l-threo-hex-2-enonicacid,gamma-lactone
  • L-Xyloascorbic acid
  • l-xyloascorbicacid
  • Mediatric component of
  • Meri-C