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47612

Sigma-Aldrich

Folinic acid calcium salt hydrate

BioXtra, ≥99.0% (HPLC)

Synonym(s):

5-Formyl-5,6,7,8-tetrahydrofolic acid calcium salt, 5-Formyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid calcium salt, 5-HCO-H4PteGlu, Calcium folinate, Citrovorum factor calcium salt, Leucovorin calcium salt

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About This Item

Empirical Formula (Hill Notation):
C20H21CaN7O7 · xH2O
CAS Number:
Molecular Weight:
511.50 (anhydrous basis)
Beilstein:
5723924
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.28

biological source

synthetic

Quality Level

product line

BioXtra

Assay

≥99.0% (HPLC)

form

powder or crystals

technique(s)

cell culture | mammalian: suitable

color

white to faint yellow

mp

240-250 °C

application(s)

cell analysis

SMILES string

[Ca++].[H]O[H].[H]C(=O)N1C(CNc2ccc(cc2)C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)CNc3nc(N)nc(O)c13

InChI

1S/C20H23N7O7.Ca/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30;/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32);/q;+2/p-2/t12?,13-;/m0./s1

InChI key

KVUAALJSMIVURS-ZEDZUCNESA-L

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General description

Calcium salt of the (6R,S)-mixture of diastereomers of 5-formyl-5,6,7,8-tetrahydrofolate.
Folinic acid, also called as calcium leucovorin, is usually available as an amorphous powder and lacks odor. This activated form of vitamin B9 is off-white to light beige in color. Folic acid (FA) is a water-soluble vitamin. Folinic acid is the 5-formyl derivative of tetrahydrofolic acid and is the reduced form of folic acid.

Application

Folinic acid calcium salt hydrate has been used in the preparation of topical 1% and 2.5% folinic acid creams for use in wound healing studies. It has also been used as a component in the chemically defined-Chinese hamster ovary medium (CD-CHO) to culture CHO DUKX B11.
Calcium folinate offsets the effects of folic acid antagonists that act by binding dihydrofolate reductase and blocking the conversion of folic acid to tetrahydrofolate. In medicine, calcium folinate is used after treatment with methotrexate to reduce the toxicity of the methotrexate. Calcium folinate is also used to enhance the cytotoxic effect of 5-fluorouracil in the treatment of cancer.

Biochem/physiol Actions

Folinic acid serves as a cofactor and participates in one-carbon-transfer reactions. It helps in improving wound healing in rats. Folinic acid plays a major role in children with autism to enhance verbal communication.

Other Notes

Review

Pictograms

Health hazardExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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L.O. Pont et al.
Anal. Profiles Drug Subst., 8, 315-315 (1979)
Nutritional Regulation of Mitochondrial Function
Mitochondria, 93-126 (2019)
Methotrexate-induced cytotoxicity and genotoxicity in germ cells of mice: Intervention of folic and folinic acid
Padmanabhan S, et al.
Mutation Research, 673(1), 43-52 (2009)
Folinic acid improves verbal communication in children with autism and language impairment: a randomized double-blind placebo-controlled trial
Frye RE, et al.
Molecular Psychiatry, 23, 247-247 (2018)
Topical folinic acid enhances wound healing in rat model
Duman N, et al.
Advances in Medical Sciences, 63(2), 347-352 (2018)

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