Vinigrol | CAS#111025-83-3 | antihypertensive

MedKoo Cat#: 585389 | Name: Vinigrol

Description:

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

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

Chemical Structure

Vinigrol

CAS#111025-83-3

Theoretical Analysis

MedKoo Cat#: 585389

Name: Vinigrol

CAS#: 111025-83-3

Chemical Formula: C20H34O3

Exact Mass: 322.2508

Molecular Weight: 322.49

Elemental Analysis: C, 74.49; H, 10.63; O, 14.88

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

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]

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 322.49 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: 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.