34420-19-4

Basic information

• Product Name: Lathyrol
• Synonyms: (1aR,2E,4aR,7aR,11aS)-1,1a,4,4a,5,6,7,7a,8,10,11,11a-Dodecahydro-1,1,3,6α-tetramethyl-4-oxo-9-methylene-9H-cyclopenta[a]cyclopropa[f]cycloundecene-4aα,7α,8β-triol;(1aR,2E,4aR,6S,7S,7aR,8R,11aS)-1,1a,4a,5,6,7,7a,8,9,10,11,11a-Dodecahydro-4a,7,8-trihydroxy-1,1,3,6-tetramethyl-9-methylene-4H-cyclopenta[a]cyclopropa[f]cycloundecen-4-one
• CAS NO: 34420-19-4
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.45
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 34420-19-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 503.537 °C at 760 mmHg
• Flash Point: 272.422 °C
• Appearance: /
• Density: 1.180
• Vapor Pressure: 3.01E-12mmHg at 25°C
• Refractive Index: 1.566
• Storage Temp.: 2-8°C
• PKA: 12.17±0.70(Predicted)
• CAS DataBase Reference: Lathyrol(CAS DataBase Reference)
• NIST Chemistry Reference: Lathyrol(34420-19-4)
• EPA Substance Registry System: Lathyrol(34420-19-4)

Safety Data

• Hazardous Substances Data: 34420-19-4(Hazardous Substances Data)

Usage

Uses

Lathyrol is a chemical constituent found in the seeds of Euphorbia lathyris that could induce leukemia in SWR mice.

InChI:InChI=1/C20H30O4/c1-10-6-7-13-14(19(13,4)5)8-11(2)18(23)20(24)9-12(3)17(22)15(20)16(10)21/h8,12-17,21-22,24H,1,6-7,9H2,2-5H3/b11-8+/t12-,13-,14+,15-,16-,17-,20+/m0/s1

Upstream product

• 1613699-95-8 3,5,15-tri-O-acetyllathyrol 
• 247099-01-0 lathyrol-3-phenylacetate-5,15-diacetate 

Relevant articles and documents

Further new diterpene esters from the irritant and cocarcinogenic seed oil and latex of the caper spurge (Euphorbia lathyris L.).

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Lathyrol and epoxylathyrol derivatives: Modulation of Cdr1p and Mdr1p drug-efflux transporters of Candida albicans in Saccharomyces cerevisiae model

Macrocyclic diterpenes were previously found to be able to modulate the efflux pump activity of Candida albicans multidrug transporters. Most of these compounds were jatrophanes, but only a few number of lathyrane-type diterpenes was evaluated. Therefore, the aim of this study was to evaluate the ability of nineteen structurally-related lathyrane diterpenes (1–19) to overcome the drug-efflux activity of Cdr1p and Mdr1p transporters of C. albicans, and get some insights on their structure-activity relationships. The transport assay was performed by monitoring Nile Red (NR) efflux in a Saccharomyces cerevisiae strain overexpressing the referred efflux pumps from C. albicans. Moreover, a chemosensitization assay was performed in order to evaluate the type of interaction between the inhibitory compounds and the antifungal drug fluconazole. Compounds 1–13 were previously isolated from Euphorbia boetica or obtained by derivatization, and compounds 14–19 were prepared by chemical transformations of compound 4. In the transport assays, compounds 14–19 revealed the strongest inhibitory activity of the Cdr1p efflux pump, ranging from 65 to 85%. Concerning Mdr1p efflux pump, the most active compounds were 1, 3, 6, 8, and 12 (75–85%). When used in combination with fluconazole, epoxyboetirane K (2) and euphoboetirane N (18) revealed synergistic effects in the AD-CDR1 yeast strain, overexpressing the Cdr1p transporter, through their ability to reduce the effective concentration of the antifungal drug by 23- and 52-fold, respectively.

Lathyrane Diterpenoids as Novel hPXR Agonists: Isolation, Structural Modification, and Structure-Activity Relationships

Pregnane X receptor (PXR) that orchestrates the intricate network of xeno- and endobiotic metabolism is considered as a promising therapeutic target for cholestasis. In this study, the human PXR (hPXR) agonistic bioassay-guided isolation of Euphorbia lathyris followed by the structural modification led to the construction of a lathyrane diterpenoid library (1-34). Subsequent assay of this library led to the identification of a series of potent hPXR agonists, showing better efficacy than that of typical hPXR agonist, rifampicin. The most active compound, 8, could dose-dependently activate hPXR at micromolar concentrations and significantly up-regulate the expressions of PXR downstream genes CYP3A4, CYP2B6, and MDR1. The structure-activity relationships (SARs) studied in combination with molecular modeling suggested that acyloxy at C-7 and the presence of 14-carbonyl were essential to the activity. These findings suggested that lathyrane diterpenoids could serve as a new type of hPXR agonist for future anticholestasis drug development.