(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one

• ChemBase ID: 12
• Molecular Formular: C6H8O6
• Molecular Mass: 176.12412
• Monoisotopic Mass: 176.03208798
• SMILES: O1C(=O)C(=C(O)[C@H]1[C@H](CO)O)O
• Canonical SMILES: OC[C@@H]([C@H]1OC(=O)C(=C1O)O)O
• InChI: InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1
• InChIKey: CIWBSHSKHKDKBQ-JLAZNSOCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
• IUPAC Traditional name: vitamin C
• Brand Name: Adenex; Allercorb; Antiscorbic Vitamin; Antiscorbutic Vitamin; Arco-Cee; Ascoltin; Ascor-B.I.D.; Ascorb; Ascorbajen; Ascorbicab; Ascorbicap; Ascorbicin; Ascorbin; Ascorbutina; Ascorin; Ascorteal; Ascorvit; C-Level; C-Long; C-Quin; C-Span; C-Vimin; Cantan; Cantaxin; Catavin C; Ce Lent; Cebicure; Cebid; Cebion; Cebione; Cecon; Cee-Caps Td; Cee-Vite; Cegiolan; Ceglion; Celaskon; Celin; Cemagyl; Cemill; Cenetone; Cenolate; Cereon; Cergona; Cescorbat; Cetamid; Cetane; Cetane-Caps Tc; Cetane-Caps Td; Cetebe; Cetemican; Cevalin; Cevatine; Cevex; Cevi-Bid; Cevimin; Cevital; Cevitamic Acid; Cevitamin; Cevitan; Cevitex; Cewin; Ciamin; Cipca; Citriscorb; Colascor; Concemin; Davitamon C; Duoscorb; Hicee; Hybrin; IDO-C; Kyselina Askorbova; Laroscorbine; Lemascorb; Liqui-Cee; Meri-C; Natrascorb; Planavit C; Proscorbin; Redoxon; Ribena; Roscorbic; Scorbacid; Scorbu-C; Secorbate; Sodascorbate; Testascorbic; Vicelat; Vicin; Vicomin C; Viforcit; Viscorin; Vitace; Vitacee; Vitacimin; Vitacin; Vitamisin; Vitascorbol; Xitix
• Synonyms: Acidum ascorbicum; L-(+)-Ascorbic acid, ACS; L-(+)-Ascorbic acid; (R)-5-((S)-1,2-Dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one; L-Ascorbic acid; Vitamin C; Ascorbic acid; L-Threoascorbic acid; Antiscorbutic factor; AA; Ascorbic Acid; L-Ascorbate; L-Ascorbic Acid; Ascorbate; L-Lyxoascorbic Acid; L-Xyloascorbic Acid; Vitamin C; L-(+)-抗坏血酸, ACS; L-(+)-抗坏血酸; L-(+)-抗坏血酸维生素C; L-维生素 C; 抗坏血病因子; 维生素 C; L-抗坏血酸

Database IDs

• CAS Number: 50-81-7
• EC Number: 200-066-2
• MDL Number: MFCD00064328
• Beilstein Number: 84272
• Merck Index: 14830
• PubChem SID: 24890632; 24890417; 24891432; 24890107; 24855464; 24891246; 24890106; 24890649; 160963475; 24900863; 24890105; 24891042; 24871532; 24890635; 24890875; 24859847; 24890857
• PubChem CID: 54670067; 5785
• CHEBI ID: 29073
• ATC CODE: G01AD03; A11GA01; S01XA15; A11G
• CHEMBL: 196
• Chemspider ID: 10189562
• DrugBank ID: DB00126
• FEMA ID: 2109
• KEGG ID: D00018
• Unique Ingredient Identifier: PQ6CK8PD0R
• Wikipedia Title: Ascorbic_acid; Vitamin_C
• E Number: E300

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.3599176
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.082243
• LogD (pH = 7.4): -4.8322015
• Log P: -1.9135588
• Molar Refractivity: 37.0321 cm^3
• Polarizability: 14.376429 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.58
• LOG S: 0.14
• Solubility (Water): 2.45e+02 g/l

PROPERTIES

Physical Property

• Solubility: 10 g/L in glycerol; 20 g/L in ethanol; 330 g/L in water; 40 g/L; 50 g/L in propylene glycol; H2O: soluble0.5 M, clear, colorless; H2O: soluble1 M at 20 °C, clear, colorless; H2O: soluble10 mg/mL; H2O: soluble50 mg/mL at 20 °C, clear, almost colorless; insoluble in diethyl ether, chloroform, benzene, petroleum ether, oils, fats in other solvents
• Apperance: powder; Powder; White or light yellow solid; white to off-white crystalline; white to off-white powder; white to slightly yellow crystalline
• Melting Point: 190 - 192°C (decomp.); 190°C (374°F); 190-193°C dec.; 190-194 °C (dec.); ca 191°C dec.
• Boiling Point: 553°C (1027.4°F)
• Density: 1.65; 1.65 g/cm^3; 1.694 g/cm^3
• Optical Rotation: [α]20/D +20.5 to +21.5°, c = 10% in H2O; [α]20/D +21±0.5°, c = 10% in H2O; [α]25/D +20.5 to +21.5° in H2O; [α]25/D 19.0 to 23.0°, c = 10% in H2O; +21 (c=10 in water)
• Hydrophobicity(logP): -0.5
• pKa: 4.10 (first), 11.6 (second)
• pH: 1.0-2.5 (25 °C, 1 M in H2O); 2.1-2.6 (20 °C, 5%); 2.2-2.5 (25 °C, 50 mg/mL in H2O)

Safety Information

• RTECS: CI7650000
• German water hazard class: 1
• TSCA Listed: 是
• NFPA704:
  

  1

  1

  0
• LD50: 11.9 g/kg (oral, rat)
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C
• Regulation Compliance: FCC; FDA 21 CFR (172.280); FDA 21 CFR (182.3013); FDA 21 CFR (182.8013)

Pharmacology Properties

• Admin Routes: oral
• Bioavailability: rapid & complete
• Excretion: renal
• Half Life: varies according to plasma concentration
• Protein Bound: negligible
• Legal Status: general public availability
• Pregnancy Category: A
• Gene Information: human ... SLC23A2(9962)
• Allergens: no known allergens

Product Information

• Purity: ≥98%; ≥99%; ≥99.0%; ≥99.0% (RT); ≥99.5% (RT); ≥99.9998% (metals basis); 98%; 98+%; 99%; 99.7-100.5% (oxidimetric); 99+%
• Grade: ACS reagent; ACS reagent, reag. ISO, reag. Ph. Eur.; analytical standard; JIS special grade; Ph Eur; puriss. p.a.; reagent grade; TraceSELECT®
• Packaging: ampule of 1000 mg
• Suitability: cell culture tested; complies for appearance of solution; meets USP testing specifications; passes test for identity (IR); plant cell culture tested; suitable for cell culture; suitable for plant cell culture
• Ignition Residue: <0.1%; ≤0.05% (as SO4); ≤0.1%; ≤0.1% (as SO4)
• Impurities: ≤0.0005% Phosphorus (P); ≤0.001% heavy metals (as Pb); ≤0.1% Insoluble matter; insoluble matter, passes filter test; related substances, in accordance (HPLC)
• Cation Traces: Ag: ≤0.01 mg/kg; Al: ≤0.0005%; Al: ≤0.05 mg/kg; Al: ≤5 mg/kg; As: ≤0.005 mg/kg; As: ≤0.1 mg/kg; As: ≤1 mg/kg; Au: ≤0.01 mg/kg; Ba: ≤0.01 mg/kg; Ba: ≤5 mg/kg; Be: ≤0.01 mg/kg; Bi: ≤0.01 mg/kg; Bi: ≤5 mg/kg; Ca: ≤0.0005%; Ca: ≤0.1 mg/kg; Ca: ≤10 mg/kg; Cd: ≤0.01 mg/kg; Cd: ≤5 mg/kg; Ce: ≤0.01 mg/kg; Co: ≤0.01 mg/kg; Co: ≤5 mg/kg; Cr: ≤0.05 mg/kg; Cr: ≤5 mg/kg; Cs: ≤0.01 mg/kg; Cu: ≤0.0005%; Cu: ≤0.01 mg/kg; Cu: ≤5 mg/kg; Dy: ≤0.01 mg/kg; Er: ≤0.01 mg/kg; Eu: ≤0.01 mg/kg; Fe: ≤0.0005%; Fe: ≤0.001%; Fe: ≤0.1 mg/kg; Fe: ≤2 mg/kg; Fe: ≤5 mg/kg; Ga: ≤0.01 mg/kg; Gd: ≤0.01 mg/kg; Ge: ≤0.05 mg/kg; heavy metals (as Pb): ≤0.002%; Hf: ≤0.01 mg/kg; Hg: ≤0.01 mg/kg; Ho: ≤0.01 mg/kg; In: ≤0.01 mg/kg; Ir: ≤0.01 mg/kg; K: ≤0.005%; K: ≤0.1 mg/kg; K: ≤50 mg/kg; La: ≤0.01 mg/kg; Li: ≤0.01 mg/kg; Li: ≤5 mg/kg; Lu: ≤0.01 mg/kg; Mg: ≤0.0005%; Mg: ≤0.05 mg/kg; Mg: ≤5 mg/kg; Mn: ≤0.01 mg/kg; Mn: ≤5 mg/kg; Mo: ≤0.01 mg/kg; Mo: ≤5 mg/kg; Na: ≤0.005%; Na: ≤2 mg/kg; Na: ≤50 mg/kg; Nb: ≤0.01 mg/kg; Nd: ≤0.01 mg/kg; NH4+: ≤0.05%; NH4+: ≤5 mg/kg; Ni: ≤0.01 mg/kg; Ni: ≤5 mg/kg; Os: ≤0.01 mg/kg; Pb: ≤0.001%; Pb: ≤0.01 mg/kg; Pb: ≤5 mg/kg; Pd: ≤0.01 mg/kg; Pr: ≤0.01 mg/kg; Pt: ≤0.01 mg/kg; Rb: ≤0.01 mg/kg; Re: ≤0.01 mg/kg; Rh: ≤0.01 mg/kg; Ru: ≤0.01 mg/kg; Sb: ≤0.01 mg/kg; Sc: ≤0.05 mg/kg; Se: ≤0.01 mg/kg; Sm: ≤0.01 mg/kg; Sn: ≤0.01 mg/kg; Sr: ≤0.01 mg/kg; Sr: ≤5 mg/kg; Ta: ≤0.01 mg/kg; Tb: ≤0.01 mg/kg; Te: ≤0.01 mg/kg; Th: ≤0.01 mg/kg; Ti: ≤0.05 mg/kg; Tl: ≤0.01 mg/kg; Tm: ≤0.01 mg/kg; U: ≤0.01 mg/kg; V: ≤0.01 mg/kg; W: ≤0.01 mg/kg; Y: ≤0.01 mg/kg; Yb: ≤0.01 mg/kg; Zn: ≤0.0005%; Zn: ≤0.05 mg/kg; Zn: ≤10 mg/kg; Zn: ≤5 mg/kg; Zr: ≤0.01 mg/kg
• Antion Traces: chloride (Cl-): ≤50 mg/kg; phosphate (PO43-): ≤5 mg/kg; sulfate (SO42-): ≤0.05%; sulfate (SO42-): ≤20 mg/kg
• Sterility: γ-irradiated
• Loss on Drying: ≤0.05% loss on drying, 20 °C (HV); ≤0.1% loss on drying, 105 °C; ≤0.1% loss on drying, 110 °C
• Feature: standard type water soluble vitamin
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Product Line: BioUltra
• abs.: absorption1M/306 nm, H2O cut-off
• Pharmacopeia Traceability: traceable to BP 461; traceable to PhEur A1300000; traceable to USP 1043003
• Empirical Formula (Hill Notation): C6H8O6

DETAILS

DrugBank - DB00126

• Drug Groups: approved; nutraceutical
• Description: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant. [PubChem]
• Indication: Used to treat vitamin C deficiency, scurvy, delayed wound and bone healing, urine acidification, and in general as an antioxidant. It has also been suggested to be an effective antiviral agent.
• Pharmacology: Ascorbic Acid (vitamin C) is a water-soluble vitamin indicated for the prevention and treatment of scurvy, as ascorbic acid deficiency results in scurvy. Collagenous structures are primarily affected, and lesions develop in bones and blood vessels. Administration of ascorbic acid completely reverses the symptoms of ascorbic acid deficiency.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Ascorbic acid is reversibly oxidised (by removal of the hydrogen from the enediol group of ascorbic acid) to dehydroascorbic acid. The two forms found in body fluids are physiologically active. Some ascorbic acid is metabolized to inactive compounds including ascorbic acid-2-sulfate and oxalic acid.
• Absorption: 70% to 90%
• Half Life: 16 days (3.4 hours in people who have excess levels of vitamin C)
• Protein Binding: 25%
• References: Padayatty SJ, Katz A, Wang Y, Eck P, Kwon O, Lee JH, Chen S, Corpe C, Dutta A, Dutta SK, Levine M: Vitamin C as an antioxidant: evaluation of its role in disease prevention. J Am Coll Nutr. 2003 Feb;22(1):18-35. [Pubmed] ; Meister A: Glutathione-ascorbic acid antioxidant system in animals. J Biol Chem. 1994 Apr 1;269(13):9397-400. [Pubmed] ; Englard S, Seifter S: The biochemical functions of ascorbic acid. Annu Rev Nutr. 1986;6:365-406. [Pubmed] ; Banhegyi G, Mandl J: The hepatic glycogenoreticular system. Pathol Oncol Res. 2001;7(2):107-10. [Pubmed] ; Proctor P: Similar functions of uric acid and ascorbate in man? Nature. 1970 Nov 28;228(5274):868. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - A4403

Application
For use in cell culture applications as an antioxidant and to regenerate tocopherol.

Sigma Aldrich - A2174

Caution
储存期间颜色可变暗。

Sigma Aldrich - A2343

Biochem/physiol Actions
Ascorbic Acid, also known as Vitamin C, is a six-carbon lactone produced by plants and some animal species but not by humans and other primates. Ascorbic acid functions as an enzymatic cofactor for multiple enzymes, serving as an electron donor for monooxygenases and dioxygenases. Ascorbic acid also functions as a powerful antioxidant, particularly in regards to reactive oxygen species.

Sigma Aldrich - A5960

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Caution
储存期间颜色可变暗。
包装
10 mg in autosmp vl
Biochem/physiol Actions
Ascorbic Acid, also known as Vitamin C, is a six-carbon lactone produced by plants and some animal species but not by humans and other primates. Ascorbic acid functions as an enzymatic cofactor for multiple enzymes, serving as an electron donor for monooxygenases and dioxygenases. Ascorbic acid also functions as a powerful antioxidant, particularly in regards to reactive oxygen species.

Sigma Aldrich - A2218

Biochem/physiol Actions
Ascorbic Acid, also known as Vitamin C, is a six-carbon lactone produced by plants and some animal species but not by humans and other primates. Ascorbic acid functions as an enzymatic cofactor for multiple enzymes, serving as an electron donor for monooxygenases and dioxygenases. Ascorbic acid also functions as a powerful antioxidant, particularly in regards to reactive oxygen species.

Sigma Aldrich - 95209

Other Notes
Denaturation of proteins1; Dimeric association of E. coli RNA polymerase α subunits, studied by cleavage of single cysteine α subunits conjugated to Fe-BABE2.
Biochem/physiol Actions
L-Ascorbic acid (Vitamin C) is a water soluble molecule use in a wide variety of applications, including cell culture, as a reducing agent that helps reduce oxidative stress. L-Ascorbate can be regenerated by biological systems.

Sigma Aldrich - A4544

Biochem/physiol Actions
Ascorbic Acid, also known as Vitamin C, is a six-carbon lactone produced by plants and some animal species but not by humans and other primates. Ascorbic acid functions as an enzymatic cofactor for multiple enzymes, serving as an electron donor for monooxygenases and dioxygenases. Ascorbic acid also functions as a powerful antioxidant, particularly in regards to reactive oxygen species.

Sigma Aldrich - A7506

Application
抗氧化剂。
Caution
储存期间颜色可变暗。
Biochem/physiol Actions
Ascorbic Acid, also known as Vitamin C, is a six-carbon lactone produced by plants and some animal species but not by humans and other primates. Ascorbic acid functions as an enzymatic cofactor for multiple enzymes, serving as an electron donor for monooxygenases and dioxygenases. Ascorbic acid also functions as a powerful antioxidant, particularly in regards to reactive oxygen species.

Sigma Aldrich - A0278

Application
抗氧化剂。
Caution
储存期间颜色可变暗。
Biochem/physiol Actions
Ascorbic Acid, also known as Vitamin C, is a six-carbon lactone produced by plants and some animal species but not by humans and other primates. Ascorbic acid functions as an enzymatic cofactor for multiple enzymes, serving as an electron donor for monooxygenases and dioxygenases. Ascorbic acid also functions as a powerful antioxidant, particularly in regards to reactive oxygen species.

Sigma Aldrich - W210901

Packaging
1 kg in poly bottle
1 sample in glass bottle
10, 25 kg in fiber drum

Sigma Aldrich - 05878

Legal Information
TraceSELECT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 95212

Biochem/physiol Actions
Ascorbic Acid, also known as Vitamin C, is a six-carbon lactone produced by plants and some animal species but not by humans and other primates. Ascorbic acid functions as an enzymatic cofactor for multiple enzymes, serving as an electron donor for monooxygenases and dioxygenases. Ascorbic acid also functions as a powerful antioxidant, particularly in regards to reactive oxygen species.

Sigma Aldrich - A92902

Packaging
2 kg in poly drum
25, 100, 500 g in poly bottle
Biochem/physiol Actions
Ascorbic Acid, also known as Vitamin C, is a six-carbon lactone produced by plants and some animal species but not by humans and other primates. Ascorbic acid functions as an enzymatic cofactor for multiple enzymes, serving as an electron donor for monooxygenases and dioxygenases. Ascorbic acid also functions as a powerful antioxidant, particularly in regards to reactive oxygen species.

Sigma Aldrich - 01-6739

Suitability
environmental analysis

Sigma Aldrich - 95210

Other Notes
Starting material for the synthesis of chiral building blocks 1,2,3,4

Sigma Aldrich - 255564

Packaging
100, 500 g in poly bottle
5 g in glass bottle
Application
Its immunostimulant derivatives play an important role in cell regulation.1

REFERENCES

• Padayatty SJ, Katz A, Wang Y, Eck P, Kwon O, Lee JH, Chen S, Corpe C, Dutta A, Dutta SK, Levine M: Vitamin C as an antioxidant: evaluation of its role in disease prevention. J Am Coll Nutr. 2003 Feb;22(1):18-35. Pubmed
• Meister A: Glutathione-ascorbic acid antioxidant system in animals. J Biol Chem. 1994 Apr 1;269(13):9397-400. Pubmed
• Englard S, Seifter S: The biochemical functions of ascorbic acid. Annu Rev Nutr. 1986;6:365-406. Pubmed
• Banhegyi G, Mandl J: The hepatic glycogenoreticular system. Pathol Oncol Res. 2001;7(2):107-10. Pubmed
• Proctor P: Similar functions of uric acid and ascorbate in man? Nature. 1970 Nov 28;228(5274):868. Pubmed