Lithium lactate

Lithium lactate
Names
	Other names Lithium 2-hydroxypropanoate
Identifiers
CAS Number	867-55-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	107852;
ECHA InfoCard	100.011.602
EC Number	212-761-8;
PubChem CID	24867598;
CompTox Dashboard (EPA)	DTXSID00883597;
	InChI InChI=1S/C3H6O3.Li/c1-2(4)3(5)6;/h2,4H,1H3,(H,5,6);/q;+1/p-1 Key: GKQWYZBANWAFMQ-UHFFFAOYSA-M;
	SMILES [Li+].CC(C(=O)[O-])O;
Properties
Chemical formula	C; 3H; 5LiO; 3
Molar mass	96.01
Appearance	Amorphous solid
Density	g/cm3
Melting point	300 °C (572 °F; 573 K)
Solubility in water	Very soluble
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Other cations	Sodium lactate
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Lithium lactate is a chemical compound, a salt of lithium and lactic acid with the formula CH₃CH(OH)COOLi,^[4] an amorphous solid, very soluble in water.^[5]

Synthesis

Synthesis is by neutralization of lactic acid with lithium hydroxide:

LiOH + CH₃CH(OH)COOH → CH₃CH(OH)COOLi + H₂O

Physical properties

Lithium lactate forms an amorphous solid.

It dissolves very well in water^[6] and organic solvents.

The compound demonstrates optical isomerism.

Lithium lactate emits acrid smoke when heated to decomposition.^[7]

Chemical properties

Lithium lactate reacts with triphosgene to obtain lactic acid-O-internal anhydride.^[8] It can be used as a precursor to prepare Li₄SiO₄,^[9] Li₄Ti₅O₁₂/C^[10] and other materials.

Use

Lithium lactate is part of drugs that promote the excretion of uric acid from the body.^[11] This is linked to a historical use of lithium to help remove uric acid, but it was later shown that doses needed for it to work would be toxic.^[12]

It is also used as a mood stabilizer.^[13]^{[failed verification]}

References

^ "867-55-0 CAS | LITHIUM LACTATE | Laboratory Chemicals | Article No. 04444". Loba Chemie. Retrieved 17 January 2022.
^ "27848-80-2 - L-(+)-Lactic acid lithium salt, Thermo Scientific - Lithium Lactate - J18160 - Alfa Aesar". Alfa Aesar. Retrieved 17 January 2022.
^ "Lithium lactate". pubchem.ncbi.nlm.nih.gov. Retrieved 22 January 2022.
^ "Lithium Lactate". American Elements. Retrieved 17 January 2022.
^ "Lithium lactate". Sigma Aldrich. Retrieved 17 January 2022.
^ Lewis, Robert A. (31 May 2016). Hawley's Condensed Chemical Dictionary. John Wiley & Sons. p. 840. ISBN 978-1-118-13515-0. Retrieved 17 January 2022.
^ Lewis, Richard J. (13 June 2008). Hazardous Chemicals Desk Reference. John Wiley & Sons. p. 844. ISBN 978-0-470-18024-2. Retrieved 17 January 2022.
^ Nölle, Roman; Schmiegel, Jan-Patrick; Winter, Martin; Placke, Tobias (14 January 2020). "Tailoring Electrolyte Additives with Synergistic Functional Moieties for Silicon Negative Electrode-Based Lithium Ion Batteries: A Case Study on Lactic Acid O-Carboxyanhydride". Chemistry of Materials. 32 (1): 173–185. doi:10.1021/acs.chemmater.9b03173. ISSN 0897-4756. S2CID 213665815. Retrieved 23 January 2022.
^ Yang, Xinwei; Liu, Wenqiang; Sun, Jian; Hu, Yingchao; Wang, Wenyu; Chen, Hongqiang; Zhang, Yang; Li, Xian; Xu, Minghou (2016). "Preparation of Novel Li4SiO4 Sorbents with Superior Performance at Low CO2 Concentration". ChemSusChem. 9 (13): 1607–1613. doi:10.1002/cssc.201501699. ISSN 1864-564X. PMID 27312486. Retrieved 23 January 2022.
^ Stenina, I. A.; Sobolev, A. N.; Kuz’mina, A. A.; Kulova, T. L.; Yaroslavtsev, A. B. (1 August 2019). "Effect of the Carbon Source on the Electrochemical Properties of Li4Ti5O12/C Composites Prepared by Solid-State Synthesis". Inorganic Materials. 55 (8): 803–809. doi:10.1134/S0020168519080156. ISSN 1608-3172. S2CID 201715779. Retrieved 23 January 2022.
^ Handler, J. S. (October 1, 1960). "The role of lactic acid in the reduced excretion of uric acid in toxemia of pregnancy". The Journal of Clinical Investigation. 39 (10): 1526–1532. doi:10.1172/JCI104172. ISSN 0021-9738. PMC 441887. PMID 13711188.
^ Marmol F (December 2008). "Lithium: bipolar disorder and neurodegenerative diseases Possible cellular mechanisms of the therapeutic effects of lithium". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 32 (8): 1761–1771. doi:10.1016/j.pnpbp.2008.08.012. PMID 18789369. S2CID 25861243.
^ Wang, Quan; Xu, Xinxiu; Li, Jun; Liu, Jing; Gu, Haifeng; Zhang, Ru; Chen, Jiekai; Kuang, Yin; Fei, Jian; Jiang, Cong; Wang, Ping; Pei, Duanqing; Ding, Sheng; Xie, Xin (July 5, 2011). "Lithium, an anti-psychotic drug, greatly enhances the generation of induced pluripotent stem cells". Cell Research. 21 (10): 1424–1435. doi:10.1038/cr.2011.108. ISSN 1748-7838. PMC 3193456. PMID 21727907.

[1] "867-55-0 CAS | LITHIUM LACTATE | Laboratory Chemicals | Article No. 04444". Loba Chemie. Retrieved 17 January 2022.

[2] "27848-80-2 - L-(+)-Lactic acid lithium salt, Thermo Scientific - Lithium Lactate - J18160 - Alfa Aesar". Alfa Aesar. Retrieved 17 January 2022.

[3] "Lithium lactate". pubchem.ncbi.nlm.nih.gov. Retrieved 22 January 2022.

[AA-4] "Lithium Lactate". American Elements. Retrieved 17 January 2022.

[5] "Lithium lactate". Sigma Aldrich. Retrieved 17 January 2022.

[6] Lewis, Robert A. (31 May 2016). Hawley's Condensed Chemical Dictionary. John Wiley & Sons. p. 840. ISBN 978-1-118-13515-0. Retrieved 17 January 2022.

[7] Lewis, Richard J. (13 June 2008). Hazardous Chemicals Desk Reference. John Wiley & Sons. p. 844. ISBN 978-0-470-18024-2. Retrieved 17 January 2022.

[8] Nölle, Roman; Schmiegel, Jan-Patrick; Winter, Martin; Placke, Tobias (14 January 2020). "Tailoring Electrolyte Additives with Synergistic Functional Moieties for Silicon Negative Electrode-Based Lithium Ion Batteries: A Case Study on Lactic Acid O-Carboxyanhydride". Chemistry of Materials. 32 (1): 173–185. doi:10.1021/acs.chemmater.9b03173. ISSN 0897-4756. S2CID 213665815. Retrieved 23 January 2022.

[9] Yang, Xinwei; Liu, Wenqiang; Sun, Jian; Hu, Yingchao; Wang, Wenyu; Chen, Hongqiang; Zhang, Yang; Li, Xian; Xu, Minghou (2016). "Preparation of Novel Li4SiO4 Sorbents with Superior Performance at Low CO2 Concentration". ChemSusChem. 9 (13): 1607–1613. doi:10.1002/cssc.201501699. ISSN 1864-564X. PMID 27312486. Retrieved 23 January 2022.

[10] Stenina, I. A.; Sobolev, A. N.; Kuz’mina, A. A.; Kulova, T. L.; Yaroslavtsev, A. B. (1 August 2019). "Effect of the Carbon Source on the Electrochemical Properties of Li4Ti5O12/C Composites Prepared by Solid-State Synthesis". Inorganic Materials. 55 (8): 803–809. doi:10.1134/S0020168519080156. ISSN 1608-3172. S2CID 201715779. Retrieved 23 January 2022.

[11] Handler, J. S. (October 1, 1960). "The role of lactic acid in the reduced excretion of uric acid in toxemia of pregnancy". The Journal of Clinical Investigation. 39 (10): 1526–1532. doi:10.1172/JCI104172. ISSN 0021-9738. PMC 441887. PMID 13711188.

[pmid_18789369-12] Marmol F (December 2008). "Lithium: bipolar disorder and neurodegenerative diseases Possible cellular mechanisms of the therapeutic effects of lithium". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 32 (8): 1761–1771. doi:10.1016/j.pnpbp.2008.08.012. PMID 18789369. S2CID 25861243.

[13] Wang, Quan; Xu, Xinxiu; Li, Jun; Liu, Jing; Gu, Haifeng; Zhang, Ru; Chen, Jiekai; Kuang, Yin; Fei, Jian; Jiang, Cong; Wang, Ping; Pei, Duanqing; Ding, Sheng; Xie, Xin (July 5, 2011). "Lithium, an anti-psychotic drug, greatly enhances the generation of induced pluripotent stem cells". Cell Research. 21 (10): 1424–1435. doi:10.1038/cr.2011.108. ISSN 1748-7838. PMC 3193456. PMID 21727907.

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v t e Lithium compounds (list)
Inorganic (list)	Li₂ LiAlCl₄ Li_1+xAl_xGe_2−x(PO₄)₃ LiAlH₄ LiAlO₂ LiAl_1+xTi_2−x(PO₄)₃ LiAs LiAsF₆ Li₃AsO₄ LiAt Li[AuCl₄] LiB(C₂O₄)₂ LiB(C₆F₅)₄ LiWF₆ LiBF₄ LiBH₄ LiBO₂ LiB₃O₅ Li₂B₄O₇ LiAsF₆ Li₂SnF₆ Li₂TiF₆ Li₂ZrF₆ Li₂B₄O₇·5H₂O LiBSi₂ LiBr LiBr·2H₂O LiBrO LiBrO₂ LiBrO₃ LiBrO₄ Li₂C₂ LiCF₃SO₃ CH₃CH(OH)COOLi LiC₂H₂ClO₂ LiC₂H₃IO₂ Li(CH₃)₂N LiCHO₂ LiCH₃O LiC₂H₅O LiCN Li₂CN₂ LiCNO Li₂CO₃ Li₂C₂O₄ LiCl LiCl·H₂O LiClO LiFO LiClO₂ LiClO₃ LiClO₄ LiCoO₂ Li₂CrO₄ Li₂CrO₄·2H₂O Li₂Cr₂O₇ CsLiB₆O₁₀ LiD LiF Li₂F LiF₄Al Li₃F₆Al FLiBe LiFePO₄ FLiNaK LiGaH₄ Li₂GeF₆ Li₂GeO₃ LiGe₂(PO₄)₃ LiH LiH₂AsO₄ Li₂HAsO₄ LiHCO₃ Li₃H(CO₃)₂ LiH₂PO₃ LiH₂PO₄ LiHSO₃ LiHSO₄ LiHe LiI LiIO LiIO₂ LiIO₃ LiIO₄ Li₂IrO₃ Li₇La₃Zr₂O₁₂ LiMn₂O₄ Li₂MoO₄ Li_0.9Mo₆O₁₇ LiN₃ Li₃N LiNH₂ Li₂NH LiNO₂ LiNO₃ LiNO₃·H₂O Li₂N₂O₂ LiNa Li₂NaPO₃ LiNaNO₂ LiNbO₃ Li₂NbO₃ LiO⁻ LiO₂ LiO₃ Li₂O Li₂O₂ LiOH Li₃P LiPF₆ Li₃PO₄ Li₂HPO₃ Li₂HPO₄ Li₃PO₃ Li₃PO₄ Li₂Po Li₂PtO₃ Li₂RuO₃ Li₂S LiSCN LiSH LiSO₃F Li₂SO₃ Li₂SO₄ Li[SbF₆] Li₂Se Li₂SeO₃ Li₂SeO₄ LiSi Li₂SiF₆ Li₄SiO₄ Li₂SiO₃ Li₂Si₂O₅ LiTaO₃ Li₂Te LiTe₃ Li₂TeO₃ Li₂TeO₄ Li₂TiO₃ Li₄Ti₅O₁₂ LiTi₂(PO₄)₃ LiVO₃·2H₂O Li₃V₂(PO₄)₃ Li₂WO₄ LiYF₄ Neodymium-doped LiZr₂(PO₄)₃ Li₂ZrO₃
Organic (soaps)	Hemolithin (extraterrestrial protein) Organolithium reagents Gilman reagent CH₃COOLi C₄H₆LiNO₄ LiC₂F₆NO₄S₂ LiN(SiMe₃)₂ Li₃C₆H₅O₇ C₅H₅Li LiN(C₃H₇)₂ (C₆H₅)₂PLi C₁₈H₃₅LiO₃ C₆H₁₃Li C₄H₉Li CH₃CHLiCH₂CH₃ (CH₃)₃CLi C₁₂H₂₈BLi CH₃Li Li⁺C₁₀H−8 C₅H₁₁Li C₅H₃LiN₂O₄ C₆H₅Li LiC₂CH₃ LiO₂C(CH₂)₁₆CH₃ C₄H₅LiO₄ LiEt₃BH LiOC(CH₃)₃ C₉H₁₈LiN LiC₂H₃ Vinyllithium LiC ₁₁H ₂₃COO
Minerals	Amblygonite Berezanskite Brannockite Cryolithionite Darapiosite Darrellhenryite Elbaite Fluorine Elbaite Fluor-liddicoatite Emeleusite Eucryptite LiAlSiO₄ Faizievite Hectorite Hsianghualite Jadarite LiNaSiB₃O₇OH Keatite Li(AlSi₂O₆) Kunzite Lavinskyite Lepidolite Lithiophilite LiMnPO₄ Lithiophosphate Li₃PO₄ Manandonite Manganoneptunite Nambulite Neptunite Olympite Petalite LiAlSi₄O₁₀ Pezzottaite Cs(Be₂Li)Al₂Si₆O₁₈ Rossmanite Saliotite Sogdianite Spodumene LiAl(SiO₃)₂ Sugilite Tiptopite Tourmaline Triphylite LiFePO₄ Zabuyelite Li₂CO₃ Zektzerite Zinnwaldite
Hypothetical	Li_xBe_y HLiHe⁺ LiFHeO LiHe₂ (HeO)(LiF)₂ La_2⁄3–xLi_3xTiO₃He
Other Li-related	Aluminium–lithium alloys Heteroatom-promoted lateral lithiation LB buffer Lithium atom Lithium medication LiNi_xCo_yAl_zO₂ LiNi_xMn_yCo_zO₂ Lithium soap Lithium Triangle Lucifer yellow Magnesium–lithium alloys NASICON Environmentally friendly red light flare

Lithium lactate

Lithium lactate

Lithium lactate

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Root Wikipedia Article

Lithium lactate

Synthesis

Physical properties

Chemical properties

Use

References