Lysophosphatidic acid | CAS#22002-87-5 | phospholipid

MedKoo Cat#: 530784 | Name: Lysophosphatidic acid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lysophosphatidic acid (LPA) is a phospholipid that acts as a messenger in and around cells to regulate a variety of cellular responses. LPA has many functions, including: (1) Cell proliferation: LPA stimulates cell proliferation, migration, and survival. (2) Wound healing: LPA promotes wound healing in vivo. (3) Skin function: LPA regulates skin function and plays a role in hair follicle development, skin tumors, and scleroderma. (4) Bone development: (5) LPA4 inhibits osteogenic differentiation, while LPA1 is involved in bone defects like osteoporosis. (6) Cancer: LPA is implicated in cancer progression. (7) Neurological conditions: LPA is implicated in neuropathic pain and neurodegenerative diseases. (8). Autoimmune disease: LPA is implicated in autoimmune disease. (9) Cardiovascular diseases: LPA is implicated in cardiovascular diseases.

Chemical Structure

Lysophosphatidic acid

CAS#22002-87-5

Theoretical Analysis

MedKoo Cat#: 530784

Name: Lysophosphatidic acid

CAS#: 22002-87-5

Chemical Formula: C21H41O7P

Exact Mass: 436.2590

Molecular Weight: 436.53

Elemental Analysis: C, 57.78; H, 9.47; O, 25.66; P, 7.10

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Lysophosphatidic acid

IUPAC/Chemical Name

2-Hydroxy-3-(phosphonooxy)propyl oleate

InChi Key

WRGQSWVCFNIUNZ-KTKRTIGZSA-N

InChi Code

InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9-

SMILES Code

CCCCCCCC/C=C\CCCCCCCC(OCC(O)COP(O)(O)=O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 436.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Lei L, Su J, Chen J, Chen W, Chen X, Peng C. The role of lysophosphatidic acid in the physiology and pathology of the skin. Life Sci. 2018 Dec 22. pii: S0024-3205(18)30833-6. doi: 10.1016/j.lfs.2018.12.040. [Epub ahead of print] Review. PubMed PMID: 30584899. 2: Schmid R, Wolf K, Robering JW, Strauß S, Strissel PL, Strick R, Rübner M, Fasching PA, Horch RE, Kremer AE, Boos AM, Weigand A. ADSCs and adipocytes are the main producers in the autotaxin-lysophosphatidic acid axis of breast cancer and healthy mammary tissue in vitro. BMC Cancer. 2018 Dec 19;18(1):1273. doi: 10.1186/s12885-018-5166-z. PubMed PMID: 30567518; PubMed Central PMCID: PMC6300006. 3: Albrecht W. Lysophosphatidic acid in carcinogenesis and tumor development. EXCLI J. 2018 Oct 17;17:980-982. doi: 10.17179/excli2018-1638. eCollection 2018. PubMed PMID: 30564077; PubMed Central PMCID: PMC6295626. 4: López-Serrano C, Santos-Nogueira E, Francos-Quijorna I, Coll-Miró M, Chun J, López-Vales R. Lysophosphatidic acid receptor type 2 activation contributes to secondary damage after spinal cord injury in mice. Brain Behav Immun. 2018 Dec 11. pii: S0889-1591(18)30404-5. doi: 10.1016/j.bbi.2018.12.007. [Epub ahead of print] PubMed PMID: 30550929. 5: Song L, Zhou Z, Gan Y, Li P, Xu Y, Zhang Z, Luo F, Xu J, Zhou Q, Dai F. Long noncoding RNA OIP5-AS1 causes cisplatin resistance in osteosarcoma through inducing the LPAATβ/PI3K/AKT/mTOR signaling pathway by sponging the miR-340-5p. J Cell Biochem. 2018 Dec 11. doi: 10.1002/jcb.28244. [Epub ahead of print] PubMed PMID: 30548308. 6: Tan F, Wang J, Liu JX, Wang C, Li M, Gu Y. Electroacupuncture stimulates the proliferation and differentiation of endogenous neural stem cells in a rat model of ischemic stroke. Exp Ther Med. 2018 Dec;16(6):4943-4950. doi: 10.3892/etm.2018.6848. Epub 2018 Oct 11. PubMed PMID: 30542450; PubMed Central PMCID: PMC6257304. 7: Yatomi Y, Kurano M, Ikeda H, Igarashi K, Kano K, Aoki J. Lysophospholipids in laboratory medicine. Proc Jpn Acad Ser B Phys Biol Sci. 2018;94(10):373-389. doi: 10.2183/pjab.94.025. PubMed PMID: 30541965. 8: Tintut Y, Hsu JJ, Demer LL. Lipoproteins in Cardiovascular Calcification: Potential Targets and Challenges. Front Cardiovasc Med. 2018 Nov 23;5:172. doi: 10.3389/fcvm.2018.00172. eCollection 2018. Review. PubMed PMID: 30533416; PubMed Central PMCID: PMC6265366. 9: Poirier M, Awale M, Roelli MA, Giuffredi GT, Ruddigkeit L, Evensen L, Stooss A, Calarco S, Lorens JB, Charles RP, Reymond JL. Identifying Lysophosphatidic Acid Acyltransferase β (LPAAT-β) as the Target of a Nanomolar Angiogenesis Inhibitor from a Phenotypic Screen Using the Polypharmacology Browser PPB2. ChemMedChem. 2018 Dec 6. doi: 10.1002/cmdc.201800554. [Epub ahead of print] PubMed PMID: 30520265. 10: Radhakrishnan R, Ha JH, Jayaraman M, Liu J, Moxley KM, Isidoro C, Sood AK, Song YS, Dhanasekaran DN. Ovarian cancer cell-derived lysophosphatidic acid induces glycolytic shift and cancer-associated fibroblast-phenotype in normal and peritumoral fibroblasts. Cancer Lett. 2018 Nov 29;442:464-474. doi: 10.1016/j.canlet.2018.11.023. [Epub ahead of print] PubMed PMID: 30503552. 11: Lin S, Haque A, Raeman R, Guo L, He P, Denning TL, El-Rayes B, Moolenaar WH, Yun CC. Autotaxin determines colitis severity in mice and is secreted by B cells in the colon. FASEB J. 2018 Nov 27:fj201801415RR. doi: 10.1096/fj.201801415RR. [Epub ahead of print] PubMed PMID: 30481488. 12: Wang X, Dong HP, Wei W, Balamurugan S, Yang WD, Liu JS, Li HY. Dual expression of plastidial GPAT1 and LPAT1 regulates triacylglycerol production and the fatty acid profile in Phaeodactylum tricornutum. Biotechnol Biofuels. 2018 Nov 22;11:318. doi: 10.1186/s13068-018-1317-3. eCollection 2018. PubMed PMID: 30479663; PubMed Central PMCID: PMC6249879. 13: Mizuno H, Kihara Y, Kussrow A, Chen A, Ray M, Rivera R, Bornhop D, Chun J. Lysophospholipid G protein-coupled receptor binding parameters as determined by backscattering interferometry (BSI). J Lipid Res. 2018 Nov 21. pii: jlr.D089938. doi: 10.1194/jlr.D089938. [Epub ahead of print] PubMed PMID: 30463988. 14: Matralis AN, Afantitis A, Aidinis V. Development and therapeutic potential of autotaxin small molecule inhibitors: From bench to advanced clinical trials. Med Res Rev. 2018 Nov 21. doi: 10.1002/med.21551. [Epub ahead of print] Review. PubMed PMID: 30462853. 15: Kamiński S, Hering DM, Kordan W, Lecewicz M, Sazanov A. Influence of splicing mutation within the lysophosphatidic acid receptor 1 gene (LPAR1) on semen quality in Holstein-Friesian bulls. Pol J Vet Sci. 2018 Jun;21(2):419-421. doi: 10.24425/122611. PubMed PMID: 30450886. 16: Weng J, Jiang S, Ding L, Xu Y, Zhu X, Jin P. Autotaxin/lysophosphatidic acid signaling mediates obesity-related cardiomyopathy in mice and human subjects. J Cell Mol Med. 2018 Nov 18. doi: 10.1111/jcmm.14005. [Epub ahead of print] PubMed PMID: 30450805. 17: Sumitomo A, Siriwach R, Thumkeo D, Ito K, Nakagawa R, Tanaka N, Tanabe K, Watanabe A, Kishibe M, Ishida-Yamamoto A, Honda T, Kabashima K, Aoki J, Narumiya S. LPA induces keratinocyte differentiation and promotes skin barrier function through the LPAR1/LPAR5-RHO-ROCK-SRF axis. J Invest Dermatol. 2018 Nov 14. pii: S0022-202X(18)32815-X. doi: 10.1016/j.jid.2018.10.034. [Epub ahead of print] PubMed PMID: 30447238. 18: Cervantes-Villagrana RD, Adame-García SR, García-Jimenez I, Color-Aparicio VM, Beltran-Navarro YM, König GM, Kostenis E, Reyes-Cruz G, Gutkind JS, Vázquez-Prado J. Gβγ signaling to the chemotactic effector P-REX1 and mammalian cell migration is directly regulated by Gαq and Gα13 proteins. J Biol Chem. 2018 Nov 16. pii: jbc.RA118.006254. doi: 10.1074/jbc.RA118.006254. [Epub ahead of print] PubMed PMID: 30446620. 19: Canul-Sánchez JA, Hernández-Araiza I, Hernández-García E, Llorente I, Morales-Lázaro SL, Islas LD, Rosenbaum T. Different agonists induce distinct single-channel conductance states in TRPV1 channels. J Gen Physiol. 2018 Dec 3;150(12):1735-1746. doi: 10.1085/jgp.201812141. Epub 2018 Nov 8. PubMed PMID: 30409787; PubMed Central PMCID: PMC6279355. 20: Kuwajima K, Sumitani M, Kurano M, Kano K, Nishikawa M, Uranbileg B, Tsuchida R, Ogata T, Aoki J, Yatomi Y, Yamada Y. Lysophosphatidic acid is associated with neuropathic pain intensity in humans: An exploratory study. PLoS One. 2018 Nov 8;13(11):e0207310. doi: 10.1371/journal.pone.0207310. eCollection 2018. PubMed PMID: 30408112; PubMed Central PMCID: PMC6224112.