111025-83-3|Vinigrol|(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|-范德生物科技公司

Vinigrol

NMR下载 COA and HPLC MSDS下载
names：
(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
CAS号：
111025-83-3
MDL Number：
MF(分子式)： C20H34O3 MW(分子量)： 322.489
EINECS: Reaxys Number:
Pubchem ID: Brand:BIOFOUNT

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中文别名	(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
英文别名	Vinigrol; Antibiotic FR 900478
CAS号	111025-83-3
SMILES	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]
Inchi	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
InchiKey	UADXIAKXDDMQEN-VGZBWQSVSA-N
分子式 Formula	C20H34O3
分子量 Molecular Weight	322.489
闪点 FP
熔点 Melting point
沸点 Boiling point
Polarizability极化度
密度 Density
蒸汽压 Vapor Pressure
溶解度Solubility
性状	Solid powder
储藏条件 Storage conditions	Dry, dark and store at 0-4℃ for short term (days to weeks) or -20℃ for long term (Store correctly 2-3years).

产品说明	Vinigrol(CAS:111025-83-3):仅限应用于工业或者科学研究过程中非医疗目的，不应用于人类或动物的临床诊断以及治过程疗，该产品非药用，非食用。
Introduction	Vinigrol is an antihypertensive and platelet aggregation inhibitory agent produced by a fungus, Virgaria nigra. II.
Application1
Application2
Application3

警示图
危险性	Warning
危险性警示
安全声明
安全防护
备注

[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: PMC2787793.1

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