A lipid biosynthesis intermediate
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sn-Glycerol-3-phosphate (cyclohexyl ammonium salt hydrate)

Item No. 20729

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,2R,3-propanetriol, 1-(dihydrogen phosphate), cyclohexanamine, hydrate (1:2:X)
Synonyms
  • G3P
Molecular Formula
C3H9O6P • 2C6H13N [XH2O]
Formula Weight
370.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Ethanol: 1 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
201 nm
SMILES
OC[C@@H](O)COP(O)(O)=O.NC1CCCCC1.NC2CCCCC2.O
InChi Code
InChI=1S/2C6H13N.C3H9O6P.H2O/c2*7-6-4-2-1-3-5-6;4-1-3(5)2-9-10(6,7)8;/h2*6H,1-5,7H2;3-5H,1-2H2,(H2,6,7,8);1H2/t;;3-;/m..1./s1
InChi Key
YLAJMQDNCVUHHL-QCPCRSFHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    100 mg

    $57

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    250 mg

    $134

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    500 mg

    $238

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    Product Description

    sn-Glycerol-3-phosphate (G3P) is a phosphoric ester of glycerol that is a chemical intermediate in glycolysis and lipid metabolism.1 G3P is an integral part of the glycerophosphate shuttle, in which NADH is oxidized to regenerate NAD+ and reducing equivalents are transferred to the oxidative phosphorylation pathway.2,3,4,5 G3P is used as a substrate for lipid biosynthesis pathways in synthetic biology, in studies of reactive oxygen species in heart tissue, and to measure phosphatidic acid in cell cultures.6,7,8 It plays a vital role in systemic acquired resistance in plant immunity.9 G3P availability affects insulin production as a substrate for glycerol-3-phosphate phosphatase.10 Altered levels of G3P have been found in the saliva of Alzheimer's, frontal lobe dementia, and Lewy body disease patients.11

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Frasson, D., Boschini, R.P., Chaves, V.E., et al. The sympathetic nervous system regulates the three glycerol-3P generation pathways in white adipose tissue of fasted, diabetic and high-protein diet-fed rats. Metabolism 61(10), 1473-1485 (2012).

    2. Cottingham, I.R., and Ragan, C.I. Purification and properties of L-3-glycerophosphate dehydrogenase from pig brain mitochondria. Biochem J. 192(1), 9-18 (1980).

    3. Shen, W., Wei, Y., Dauk, M., et al. Involvement of a glycerol-3-phosphate dehydrogenase in modulating the NADH/NAD+ ratio provides evidence of a mitochondrial glycerol-3-phosphate shuttle in Arabidopsis. Plant Cell 18(2), 422-441 (2006).

    4. Yeh, J.I., Chinte, U., and Du, S.J. Structure of glycerol-3-phosphate dehydrogenase, an essential monotopic membrane enzyme involved in respiration and metabolism. Proc. Natl. Acad. Sci. USA 105(9), 3280-3285 (2008).

    5. Mráček, T., Drahota, Z., and Houštěk, J. The function and the role of the mitochondrial glycerol-3-phosphate dehydrogenase in mammalian tissues. Biochim. Biophys. Acta 1827(3), 401-410 (2013).

    6. Scott, A., Noga, M.J., De Graaf, P.T., et al. Cell-free phospholipid biosynthesis by gene-encoded enzymes reconstituted in liposomes. PLoS One 11(10), e0163058 (2016).

    7. Madungwe, N., Zilberstein, N.F., Feng, Y., et al. Critical role of mitochondrial ROS is dependent on their site of production on the electron transport chain in ischemic heart. Am. J. Cardiovasc. Dis. 6(3), 93-108 (2016).

    8. Morita, S.y., Ueda, K., and Kitagawa, S. Enzymatic measurement of phosphatidic acid in cultured cells. J. Lipid Res. 50(9), 1945-1952 (2009).

    9. Yang, Y., Zhao, J., Liu, P., et al. Glycerol-3-phosphate metabolism in wheat contributes to systemic acquired resistance against Puccinia striiformis f. sp. tritici. PLoS One 8(11), e81756 (2013).

    10. Mugabo, Y., Zhao, S., Seifried, A., et al. Identification of a mammalian glycerol-3-phosphate phosphatase: Role in metabolism and signaling in pancreatic β-cells and hepatocytes. Proc. Natl. Acad. Sci. USA E430-439 (2016).

    11. Tsuruoka, M., Hara, J., Hirayama, A., et al. Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis 34(19), 2865-2872 (2013).