An aldonic acid
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Lactobionic Acid

Item No. 18926

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-O-β-D-galactopyranosyl-D-gluconic acid, 4-O-β-D-galactopyranosyl-D-gluconic acid, δ-lactone
Synonyms
  • Galactosylgluconic Acid
Molecular Formula
C12H22O12 (for acid)
Formula Weight
358.3
Purity
≥95% (mixture of acid and lactone forms)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
OC[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C(O)=O)O1.OC[C@H]2O[C@@H](O[C@H]3[C@H](O)[C@@H](O)C(O[C@@H]3CO)=O)[C@H](O)[C@@H](O)[C@H]2O
InChi Code
InChI=1S/C12H22O12.C12H20O11/c13-1-3(15)10(7(18)8(19)11(21)22)24-12-9(20)6(17)5(16)4(2-14)23-12;13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-10,12-20H,1-2H2,(H,21,22);3-10,12-19H,1-2H2/t2*3-,4-,5+,6+,7-,8-,9-,10-,12+/m11/s1
InChi Key
GGNSUUSNYURPMG-GJEDQQNMSA-N
Shipping & Storage Information
Storage
Room temperature
Shipping
Room temperature in continental US; may vary elsewhere
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    10 g

    $49

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    25 g

    $79

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    50 g

    $130

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    100 g

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    Product Description

    Lactobionic acid is an aldonic acid that is comprised of galactose and gluconic acid and can be produced by the lactose oxidation pathway in Pseudomonas.1,2 Lactobionic acid increases the water solubility of clarithromycin and has been used as a low pH buffer for the entrapment of SYK kinase inhibitors in liposomal nanoparticles.3,4 It also has antioxidant, humectant, and metal-chelating properties.1,2 Topical administration of lactobionic acid (10% v/v) lowers the pH of the stratum corneum in mice.5 Formulations containing lactobionic acid have been used in cosmetic, pharmaceutical, biomedicine, and food applications as well as in the preservation of organs during transplantation.1,2 The free acid and δ-lactone forms of lactobionic acid are interconvertible, with acidic pH conditions favoring formation of the δ-lactone form.6 Lactobionic acid is provided as a mixture of the free acid and lactone.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Alonso, S., Rendueles, M., and Díaz, M. Bio-production of lactobionic acid: Current status, applications and future prospects. Biotechnol.Adv. 31(8), 1275-1291 (2013).

    2. Goderska, K., Szwengiel, A., and Czarnecki, Z. The utilization of Pseudomonas taetrolens to produce lactobionic acid. Appl. Biochem. Biotechnol. 173(8), 2189-2197 (2014).

    3. Zakeri-Milani, P., Mousavian-Fathi, N., Ghanbarzadeh, S., et al. Application of lactobionic acid and nonionic surfactants as solubilizing agents for parenteral formulation of clarithromycin. Adv. Pharm. Bull. 2(1), 37-42 (2012).

    4. Cely, I., Yiv, S., Yin, Q., et al. Targeting mantle cell lymphoma with anti-SYK nanoparticles. J. Anal. Oncol. 1(1), 1-9 (2012).

    5. Hachem, J.P., Roelandt, T., Schürer, N., et al. Acute acidification of stratum corneum membrane domains using polyhydroxyl acids improves lipid processing and inhibits degradation of corneodesmosomes. J. Invest. Dermatol. 130(2), 500-510 (2010).

    6. Delagustin, M.G., Gonçalves, E., Carra, S., et al. Sodium, potassium, calcium lactobionates, and lactobionic acid from Zymomonas mobilis: A novel approach about stability and stress tests. J. Pharm. Biomed. Anal. 174, 104-114 (2019).