Laurencin

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

MedKoo CAT#: 559048

CAS#: 3442-58-8

Description: Laurencin is an extract of sea hare, Aplysia dactylomela.

Chemical Structure

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Laurencin
CAS# 3442-58-8
Instruction

Theoretical Analysis

MedKoo Cat#: 559048
Name: Laurencin
CAS#: 3442-58-8
Chemical Formula: C17H23BrO3
Exact Mass: 354.08
Molecular Weight: 355.270
Elemental Analysis: C, 57.47; H, 6.53; Br, 22.49; O, 13.51

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Laurencin; NSC 122763; NSC-122763; NSC122763;

IUPAC/Chemical Name: (E)-1-((2R,7S,8R,Z)-7-bromo-8-ethyl-3,6,7,8-tetrahydro-2H-oxocin-2-yl)hex-3-en-5-yn-1-yl acetate

InChi Key: ZFYWONYUPVGTQJ-MLQIYZSFSA-N

InChi Code: InChI=1S/C17H23BrO3/c1-4-6-7-11-16(20-13(3)19)17-12-9-8-10-14(18)15(5-2)21-17/h1,6-9,14-17H,5,10-12H2,2-3H3/b7-6+,9-8-/t14-,15+,16?,17+/m0/s1

SMILES Code: C#C/C=C/CC(OC(C)=O)[C@@H]1O[C@H](CC)[C@@H](Br)C/C=C\C1

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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 355.27 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Yoshikawa K, Otsu M, Ito T, Asakawa Y, Kawano S, Hashimoto T. Aromatic constituents of Cymbidium Great Flower Marie Laurencin and their antioxidative activity. J Nat Med. 2013 Jan;67(1):217-21. doi: 10.1007/s11418-012-0653-z. Epub 2012 Mar 17. PubMed PMID: 22427197.

2: Suzuki M, Takahashi Y, Nakano S, Abe T, Masuda M, Ohnishi T, Noya Y, Seki K. An experimental approach to study the biosynthesis of brominated metabolites by the red algal genus Laurencia. Phytochemistry. 2009 Jul-Aug;70(11-12):1410-5. doi: 10.1016/j.phytochem.2009.07.038. Epub 2009 Sep 4. PubMed PMID: 19733868.

3: Adsool VA, Pansare SV. An enantioselective approach to (+)-laurencin. Org Biomol Chem. 2008 Jun 7;6(11):2011-5. doi: 10.1039/b803973a. Epub 2008 Apr 11. PubMed PMID: 18480916.

4: Li J, Suh JM, Chin E. Expedient enantioselective synthesis of the δ4-oxocene cores of (+)-laurencin and (+)-prelaureatin (‡). Org Lett. 2010 Nov 5;12(21):4712-5. doi: 10.1021/ol1021965. PubMed PMID: 20919723.

5: Kuyinu EL, Narayanan G, Nair LS, Laurencin CT. Animal models of osteoarthritis: classification, update, and measurement of outcomes. J Orthop Surg Res. 2016 Feb 2;11:19. doi: 10.1186/s13018-016-0346-5. Review. PubMed PMID: 26837951; PubMed Central PMCID: PMC4738796.

6: Baek S, Jo H, Kim H, Kim H, Kim S, Kim D. Highly stereoselective and efficient total synthesis of (+)-laurencin. Org Lett. 2005 Jan 6;7(1):75-7. PubMed PMID: 15624981.

7: Yoshikawa K, Ito T, Iseki K, Baba C, Imagawa H, Yagi Y, Morita H, Asakawa Y, Kawano S, Hashimoto T. Phenanthrene derivatives from Cymbidium Great Flower Marie Laurencin and their biological activities. J Nat Prod. 2012 Apr 27;75(4):605-9. doi: 10.1021/np200788u. Epub 2012 Mar 9. PubMed PMID: 22537363.

8: Laurencin C, Danaila T, Broussolle E, Thobois S. Initial treatment of Parkinson's disease in 2016: The 2000 consensus conference revisited. Rev Neurol (Paris). 2016 Aug - Sep;172(8-9):512-523. doi: 10.1016/j.neurol.2016.07.007. Epub 2016 Jul 29. Review. PubMed PMID: 27476416.

9: Pinn VW, Laurencin CT. The Fight for the Elimination of Racial and Ethnic Health Disparities: Acknowledging the Work and Celebrating the Life of Mr. Louis Stokes. J Racial Ethn Health Disparities. 2015 Dec;2(4):423-4. doi: 10.1007/s40615-015-0168-x. Epub 2015 Sep 28. PubMed PMID: 26863549; PubMed Central PMCID: PMC4750495.

10: Kaneko K, Washio K, Umezawa T, Matsuda F, Morikawa M, Okino T. cDNA cloning and characterization of vanadium-dependent bromoperoxidases from the red alga Laurencia nipponica. Biosci Biotechnol Biochem. 2014;78(8):1310-9. doi: 10.1080/09168451.2014.918482. Epub 2014 Jun 17. PubMed PMID: 25130731.

11: Yu X, Tang X, Gohil SV, Laurencin CT. Biomaterials for Bone Regenerative Engineering. Adv Healthc Mater. 2015 Jun 24;4(9):1268-85. doi: 10.1002/adhm.201400760. Epub 2015 Apr 7. Review. PubMed PMID: 25846250; PubMed Central PMCID: PMC4507442.

12: Ortega N, Martín VS, Martín T. An approach to lauroxanes by iterative use of Co(2)(CO)(6)-acetylenic complexes. a formal synthesis of (+)-laurencin. J Org Chem. 2010 Oct 1;75(19):6660-72. doi: 10.1021/jo101566x. PubMed PMID: 20809659.

13: Laurencin CT. Cato T. Laurencin, MD, PhD. J Natl Med Assoc. 2007 Nov;99(11):1286-7. PubMed PMID: 18020107; PubMed Central PMCID: PMC2574318.

14: Laurencin G. [The long road for psychiatric care in prisons]. Soins Psychiatr. 2016 Mar-Apr;(303):12-4. doi: 10.1016/j.spsy.2016.01.002. French. PubMed PMID: 26948192.

15: Laurencin C, Anheim M, Larrieu L, Tilikete C, Koenig M, Thobois S. Pitfalls in ataxia with ocular motor apraxia type 1: pseudodominant inheritance and very late onset. J Neurol. 2015 May;262(5):1366-8. doi: 10.1007/s00415-015-7717-4. Epub 2015 Apr 7. PubMed PMID: 25845762.

16: Crimmins MT, Emmitte KA. Total synthesis of (+)-laurencin: an asymmetric alkylation-ring-closing metathesis approach to medium ring ethers. Org Lett. 1999 Dec 16;1(12):2029-32. PubMed PMID: 10836060.

17: Loizon M, Laurencin C, Vial C, Danaila T, Thobois S. High incidence of carpal tunnel syndrome after deep brain stimulation in Parkinson's disease. J Neurol. 2016 Dec;263(12):2416-2418. Epub 2016 Sep 13. PubMed PMID: 27624119.

18: Gonem S, Berair R, Singapuri A, Hartley R, Laurencin MFM, Bacher G, Holzhauer B, Bourne M, Mistry V, Pavord ID, Mansur AH, Wardlaw AJ, Siddiqui SH, Kay RA, Brightling CE. Fevipiprant, a prostaglandin D2 receptor 2 antagonist, in patients with persistent eosinophilic asthma: a single-centre, randomised, double-blind, parallel-group, placebo-controlled trial. Lancet Respir Med. 2016 Sep;4(9):699-707. doi: 10.1016/S2213-2600(16)30179-5. Epub 2016 Aug 5. PubMed PMID: 27503237.

19: Lo KW, Kan HM, Gagnon KA, Laurencin CT. One-day treatment of small molecule 8-bromo-cyclic AMP analogue induces cell-based VEGF production for in vitro angiogenesis and osteoblastic differentiation. J Tissue Eng Regen Med. 2016 Oct;10(10):867-875. doi: 10.1002/term.1839. Epub 2013 Nov 6. PubMed PMID: 24493289; PubMed Central PMCID: PMC4497951.

20: Laurencin CT, Nair LS. REGENERATIVE ENGINEERING: APPROACHES TO LIMB REGENERATION AND OTHER GRAND CHALLENGES. Regen Eng Transl Med. 2015 Apr 1;1(1):1-3. Epub 2015 Dec 4. PubMed PMID: 26985451; PubMed Central PMCID: PMC4789288.