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MedKoo Cat#: 146358 | Name: Prolinal

Description:

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

Prolinal is a synthetic compound developed by Ono Pharmaceutical Co., Ltd., designed to inhibit prolyl endopeptidase, an enzyme involved in the metabolism of neuropeptides containing proline residues. By blocking this enzyme, prolinal aims to prevent the breakdown of these neuropeptides, which are crucial for memory and learning processes. This inhibition is particularly relevant in the context of amnesia, as it may help preserve the levels of neuropeptides necessary for cognitive function.

Chemical Structure

Prolinal
Prolinal
CAS#3760-54-1

Theoretical Analysis

MedKoo Cat#: 146358

Name: Prolinal

CAS#: 3760-54-1

Chemical Formula: C5H9NO

Exact Mass: 99.0684

Molecular Weight: 99.13

Elemental Analysis: C, 60.58; H, 9.15; N, 14.13; O, 16.14

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.
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Related CAS #
No Data
Synonym
Prolinal;
IUPAC/Chemical Name
pyrrolidine-1-carbaldehyde
InChi Key
AGRIQBHIKABLPJ-UHFFFAOYSA-N
InChi Code
1S/C5H9NO/c7-5-6-3-1-2-4-6/h5H,1-4H2
SMILES Code
O=CN1CCCC1
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 99.13 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.

Recalculate based on batch purity %
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: Russell DW, Hardison M, Genschmer KR, Szul T, Bratcher PE, Abdul Roda M, Xu X, Viera L, Blalock JE, Gaggar A, Noerager BD. Benzyloxycarbonyl-proline- prolinal (ZPP): Dual complementary roles for neutrophil inhibition. Biochem Biophys Res Commun. 2019 Oct 1;517(4):691-696. doi: 10.1016/j.bbrc.2019.07.111. Epub 2019 Aug 7. PMID: 31400851; PMCID: PMC6730661. 2: Cunningham DF, O'Connor B. Identification and initial characterisation of a N-benzyloxycarbonyl-prolyl-prolinal (Z-Pro-prolinal)-insensitive 7-(N-benzyloxycarbonyl-glycyl-prolyl-amido)-4-methylcoumarin (Z-Gly-Pro-NH- Mec)-hydrolysing peptidase in bovine serum. Eur J Biochem. 1997 Mar 15;244(3):900-3. doi: 10.1111/j.1432-1033.1997.00900.x. PMID: 9108263. 3: Puttonen KA, Lehtonen S, Raasmaja A, Männistö PT. A prolyl oligopeptidase inhibitor, Z-Pro-Prolinal, inhibits glyceraldehyde-3-phosphate dehydrogenase translocation and production of reactive oxygen species in CV1-P cells exposed to 6-hydroxydopamine. Toxicol In Vitro. 2006 Dec;20(8):1446-54. doi: 10.1016/j.tiv.2006.07.001. Epub 2006 Jul 14. PMID: 16942854. 4: Pallavicini M, Moroni B, Bolchi C, Clementi F, Fumagalli L, Gotti C, Vailati S, Valoti E, Villa L. Synthesis and alpha4beta2 nicotinic affinity of 2-pyrrolidinylmethoxyimines and prolinal oxime ethers. Bioorg Med Chem Lett. 2004 Dec 6;14(23):5827-30. doi: 10.1016/j.bmcl.2004.09.044. PMID: 15501049. 5: Yoshimoto T, Kawahara K, Matsubara F, Kado K, Tsuru D. Comparison of inhibitory effects of prolinal-containing peptide derivatives on prolyl endopeptidases from bovine brain and Flavobacterium. J Biochem. 1985 Oct;98(4):975-9. doi: 10.1093/oxfordjournals.jbchem.a135377. PMID: 3908451. 6: Ivanova EA, Zolotov NN, Voronina TA. Sravnenie vliianiia ingibitorov proliléndopeptidazy benziloksikarbonil-prolil-prolinalia i benziloksikarbonil- metionil-tsianopirrolidina na ostroe ékssudativnoe vospalenie i vistseral'nuiu bol' u mysheĭ [Comparative effect of the prolyl endopeptidase inhibitors, benzyloxycarbonyl-prolyl-prolinal and benzyloxycarbonyl-methionyl- cyanopyrrolidine, on the acute exudative inflammation and visceral pain in mice]. Biomed Khim. 2020 Sep;66(5):423-426. Russian. doi: 10.18097/PBMC20206605423. PMID: 33140738. 7: Birney YA, O'Connor BF. Purification and characterization of a Z-pro- prolinal-insensitive Z-Gly-Pro-7-amino-4-methyl coumarin-hydrolyzing peptidase from bovine serum--a new proline-specific peptidase. Protein Expr Purif. 2001 Jul;22(2):286-98. doi: 10.1006/prep.2001.1450. PMID: 11437605. 8: Mandal T, Zhao CG. Synthesis of Prolinal Dithioacetals as Catalysts for the Highly Stereoselective Michael Addition of Ketones and Aldehydes to beta- Nitrostyrenes. Tetrahedron Lett. 2007;48(33):5803-5806. doi: 10.1016/j.tetlet.2007.06.085. PMID: 18704203; PMCID: PMC2516343. 9: Bakker AV, Jung S, Spencer RW, Vinick FJ, Faraci WS. Slow tight-binding inhibition of prolyl endopeptidase by benzyloxycarbonyl-prolyl-prolinal. Biochem J. 1990 Oct 15;271(2):559-62. doi: 10.1042/bj2710559. PMID: 2241932; PMCID: PMC1149592. 10: Friedman TC, Orlowski M, Wilk S. Prolyl endopeptidase: inhibition in vivo by N-benzyloxycarbonyl-prolyl-prolinal. J Neurochem. 1984 Jan;42(1):237-41. doi: 10.1111/j.1471-4159.1984.tb09723.x. PMID: 6358414. 11: St-Pierre JF, Karttunen M, Mousseau N, Róg T, Bunker A. Use of Umbrella Sampling to Calculate the Entrance/Exit Pathway for Z-Pro-Prolinal Inhibitor in Prolyl Oligopeptidase. J Chem Theory Comput. 2011 Jun 14;7(6):1583-94. doi: 10.1021/ct1007058. Epub 2011 May 9. PMID: 26596426. 12: Briot J, Pons C, Foucher A, Goudounèche D, Gaudenzio N, Donovan M, Bernard D, Méchin MC, Simon M. Prolyl Endopeptidase Is Involved in Filaggrinolysis and Cornification. J Invest Dermatol. 2025 Jan;145(1):98-108.e15. doi: 10.1016/j.jid.2024.04.028. Epub 2024 Jun 13. PMID: 38879153. 13: Yoshimoto T, Kado K, Matsubara F, Koriyama N, Kaneto H, Tsura D. Specific inhibitors for prolyl endopeptidase and their anti-amnesic effect. J Pharmacobiodyn. 1987 Dec;10(12):730-5. doi: 10.1248/bpb1978.10.730. PMID: 3330562. 14: Wilk S, Orlowski M. Inhibition of rabbit brain prolyl endopeptidase by n-benzyloxycarbonyl-prolyl-prolinal, a transition state aldehyde inhibitor. J Neurochem. 1983 Jul;41(1):69-75. doi: 10.1111/j.1471-4159.1983.tb11815.x. PMID: 6345724. 15: Asano M, Nio N, Ariyoshi Y. Inhibition of prolyl endopeptidase by synthetic beta-casein peptides and their derivatives with a C-terminal prolinol or prolinal. Biosci Biotechnol Biochem. 1992 Jun;56(6):976-7. doi: 10.1271/bbb.56.976. PMID: 1368255. 16: Yokosawa H, Nishikata M, Ishii S. N-Benzyloxycarbonyl-valyl-prolinal, a potent inhibitor of post-proline cleaving enzyme. J Biochem. 1984 Jun;95(6):1819-21. doi: 10.1093/oxfordjournals.jbchem.a134795. PMID: 6381476. 17: Samanta S, Krause J, Mandal T, Zhao CG. Inverse-electron-demand hetero- Diels-Alder reaction of beta,gamma-unsaturated alpha-ketophosphonates catalyzed by prolinal dithioacetals. Org Lett. 2007 Jul 5;9(14):2745-8. doi: 10.1021/ol071097y. Epub 2007 Jun 9. PMID: 17559222. 18: Nishikata M, Yokosawa H, Ishii S. Synthesis and structure of prolinal- containing peptides, and their use as specific inhibitors of prolyl endopeptidases. Chem Pharm Bull (Tokyo). 1986 Jul;34(7):2931-6. doi: 10.1248/cpb.34.2931. PMID: 3533287. 19: Saito M, Hashimoto M, Kawaguchi N, Fukami H, Tanaka T, Higuchi N. Synthesis and inhibitory activity of acyl-peptidyl-prolinalderivatives toward post-proline cleaving enzyme as nootropic agents. J Enzyme Inhib. 1990;3(3):163-78. doi: 10.3109/14756369009035834. PMID: 2079633. 20: López A, Tarragó T, Giralt E. Low molecular weight inhibitors of Prolyl Oligopeptidase: a review of compounds patented from 2003 to 2010. Expert Opin Ther Pat. 2011 Jul;21(7):1023-44. doi: 10.1517/13543776.2011.577416. Epub 2011 May 3. PMID: 21539473.