Vinigrol

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MedKoo CAT#: 585389

CAS#: 111025-83-3

Description: Vinigrol is an antihypertensive and platelet aggregation inhibitory agent produced by a fungus, Virgaria nigra. II.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-02-28. Prices are subject to change without notice.

Vinigrol is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 585389
Name: Vinigrol
CAS#: 111025-83-3
Chemical Formula: C20H34O3
Exact Mass: 322.2508
Molecular Weight: 322.489
Elemental Analysis: C, 74.49; H, 10.63; O, 14.88


Synonym: Vinigrol; Antibiotic FR 900478

IUPAC/Chemical Name: (1S,2R,5S,6S,9S,10R,13S,14S)-12-(hydroxymethyl)-2,9-dimethyl-6-propan-2-yltricyclo[8.4.0.05,14]tetradec-11-ene-1,13-diol

InChi Key: UADXIAKXDDMQEN-VGZBWQSVSA-N

InChi Code: InChI=1S/C20H34O3/c1-11(2)15-7-5-12(3)17-9-14(10-21)19(22)18-16(15)8-6-13(4)20(17,18)23/h9,11-13,15-19,21-23H,5-8,10H2,1-4H3/t12-,13+,15-,16-,17-,18-,19+,20-/m0/s1

SMILES Code: O[C@@]12[C@H](C)CC[C@@]3([H])[C@H](C(C)C)CC[C@H](C)[C@]1([H])C=C(CO)[C@@H](O)[C@@]23[H]


Technical Data

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


References

1: Draghici C, Njardarson JT. Synthetic Approaches and Total Syntheses of Vinigrol, a Unique Diterpenoid. Tetrahedron. 2015 Jun 10;71(23):3775-3793. PubMed PMID: 26034329; PubMed Central PMCID: PMC4447714.

2: Yu X, Xiao L, Wang Z, Luo T. Scalable Total Synthesis of (-)-Vinigrol. J Am Chem Soc. 2019 Feb 27;141(8):3440-3443. doi: 10.1021/jacs.9b00621. Epub 2019 Feb 18. PubMed PMID: 30767520.

3: Min L, Lin X, Li CC. Asymmetric Total Synthesis of (-)-Vinigrol. J Am Chem Soc. 2019 Oct 9;141(40):15773-15778. doi: 10.1021/jacs.9b08983. Epub 2019 Sep 30. PubMed PMID: 31545036.

4: Ando T, Yoshida K, Okuhara M. Vinigrol, a novel antihypertensive and platelet aggregation inhibitory agent produced by a fungus, Virgaria nigra. II. Pharmacological characteristics. J Antibiot (Tokyo). 1988 Jan;41(1):31-5. PubMed PMID: 2831182.

5: Betkekar VV, Sayyad AA, Kaliappan KP. A domino enyne/IMDA approach to the core structure of (-) vinigrol. Org Lett. 2014 Nov 7;16(21):5540-3. doi: 10.1021/ol502497n. Epub 2014 Oct 13. PubMed PMID: 25310274.

6: Morton JG, Draghici C, Kwon LD, Njardarson JT. Rapid assembly of vinigrol's unique carbocyclic skeleton. Org Lett. 2009 Oct 15;11(20):4492-5. doi: 10.1021/ol901519k. PubMed PMID: 19728692; PubMed Central PMCID: PMC2759413.

7: Paquette LA, Efremov I. Exploratory studies aimed at a synthesis of vinigrol. 3. Evaluation of a lactone bridge as a conformational lock. J Org Chem. 2005 Jan 21;70(2):510-3. PubMed PMID: 15651794.

8: Yang Q, Njardarson JT, Draghici C, Li F. Total synthesis of vinigrol. Angew Chem Int Ed Engl. 2013 Aug 12;52(33):8648-51. doi: 10.1002/anie.201304624. Epub 2013 Jul 1. PubMed PMID: 23818094; PubMed Central PMCID: PMC3805134.

9: Yang Q, Draghici C, Njardarson JT, Li F, Smith BR, Das P. Evolution of an oxidative dearomatization enabled total synthesis of vinigrol. Org Biomol Chem. 2014 Jan 14;12(2):330-44. doi: 10.1039/c3ob42191k. PubMed PMID: 24258093; PubMed Central PMCID: PMC3901359.

10: Maimone TJ, Shi J, Ashida S, Baran PS. Total synthesis of vinigrol. J Am Chem Soc. 2009 Dec 2;131(47):17066-7. doi: 10.1021/ja908194b. PubMed PMID: 19877628; PubMed Central PMCID: PMC2787793.

11: Huters AD, Garg NK. Synthetic studies inspired by vinigrol. Chemistry. 2010 Aug 2;16(29):8586-95. doi: 10.1002/chem.201000916. Review. PubMed PMID: 20602369.

12: Wang XL, Lu YY, Wang J, Wang X, Yao HQ, Lin GQ, Sun BF. A novel synthetic approach to the bicyclo[5.3.1]undecan-11-one framework of vinigrol. Org Biomol Chem. 2014 Jun 14;12(22):3562-6. doi: 10.1039/c4ob00046c. Epub 2014 Mar 28. PubMed PMID: 24676561.

13: Grisé CM, Tessier G, Barriault L. Synthesis of the tricyclic core of vinigrol via an intramolecular Diels-Alder reaction. Org Lett. 2007 Apr 12;9(8):1545-8. Epub 2007 Mar 16. PubMed PMID: 17362025.

14: Paquette LA, Efremov I, Liu Z. Exploratory studies aimed at a synthesis of vinigrol. 2. Attempts to exploit ring-closing metathesis for construction of the central cyclooctane belt. J Org Chem. 2005 Jan 21;70(2):505-9. PubMed PMID: 15651793.

15: Souweha MS, Enright GD, Fallis AG. Vinigrol: a compact, diene-transmissive Diels-Alder strategy to the tricyclic core. Org Lett. 2007 Dec 6;9(25):5163-6. Epub 2007 Nov 14. PubMed PMID: 17999510.

16: Ando T, Tsurumi Y, Ohata N, Uchida I, Yoshida K, Okuhara M. Vinigrol, a novel antihypertensive and platelet aggregation inhibitory agent produced by a fungus, Virgaria nigra. I. Taxonomy, fermentation, isolation, physicochemical and biological properties. J Antibiot (Tokyo). 1988 Jan;41(1):25-30. PubMed PMID: 3346190.

17: Paquette LA, Liu Z, Efremov I. Exploratory studies aimed at a synthesis of vinigrol. 4. Probe of possible means for direct connection of the side arms and of ring-contraction alternatives. J Org Chem. 2005 Jan 21;70(2):514-8. PubMed PMID: 15651795.

18: Gentric L, Le Goff X, Ricard L, Hanna I. Toward the total synthesis of vinigrol: synthesis of epi-C-8-dihydrovinigrol. J Org Chem. 2009 Dec 18;74(24):9337-44. doi: 10.1021/jo901971f. PubMed PMID: 19911847.

19: Poulin J, Grisé-Bard CM, Barriault L. A formal synthesis of vinigrol. Angew Chem Int Ed Engl. 2012 Feb 27;51(9):2111-4. doi: 10.1002/anie.201108779. Epub 2012 Jan 19. PubMed PMID: 22259041.

20: Maimone TJ, Voica AF, Baran PS. A concise approach to vinigrol. Angew Chem Int Ed Engl. 2008;47(16):3054-6. doi: 10.1002/anie.200800167. PubMed PMID: 18338349.