37244-00-1

Basic information

• Product Name: vermiculine
• Synonyms: vermiculine;(3E,8S,11E,16S)-8,16-Bis(2-oxopropyl)-1,9-dioxa-3,11-cyclohexadecadiene-2,5,10,13-tetrone;(3E,8S,11E,16S)-8,16-Bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone;Vermiculin
• CAS NO: 37244-00-1
• Molecular Formula: C20H24O8
• Molecular Weight: 392.402
• Mol File: 37244-00-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 175-177 °C (decomp)
• Boiling Point: 437.13°C (rough estimate)
• Flash Point: 284.7°C
• Appearance: /
• Density: 1.2464 (rough estimate)
• Vapor Pressure: 4.73E-17mmHg at 25°C
• Refractive Index: 1.4430 (estimate)
• CAS DataBase Reference: vermiculine(CAS DataBase Reference)
• NIST Chemistry Reference: vermiculine(37244-00-1)
• EPA Substance Registry System: vermiculine(37244-00-1)

Safety Data

• Hazardous Substances Data: 37244-00-1(Hazardous Substances Data)

Usage

General Description

Vermiculite is a naturally occurring mineral compound that is commonly used in agriculture, construction, and horticulture due to its ability to retain moisture and nutrients. It is often added to soil to improve its water retention and aeration properties, making it an ideal growing medium for plants. Vermiculite is also used as a component in potting mixes and as a packing material for shipping hazardous substances. In construction, vermiculite is used as an insulating material for attics and walls due to its fire-resistant properties. However, concerns have been raised about the potential health risks associated with vermiculite that has been contaminated with asbestos, leading to regulations and guidelines for its safe use and handling.

InChI:InChI=1/C20H24O8/c1-13(21)11-17-7-3-15(23)6-10-20(26)28-18(12-14(2)22)8-4-16(24)5-9-19(25)27-17/h5-6,9-10,17-18H,3-4,7-8,11-12H2,1-2H3/b9-5-,10-6+

Upstream product

• 159955-58-5 (3E,11E)-(8S,16S)-8,16-Diallyl-1,9-dioxa-cyclohexadeca-3,11-diene-2,5,10,13-tetraone 
• 131722-62-8 1,2:5,6-dianhydro-3,4-dideoxy-erythro-hexitol 
• 159955-38-1 (5S,8S)-Dodeca-1,11-diene-5,8-diol 
• 159955-39-2 (5S,8S)-8-Benzyloxy-dodeca-1,11-dien-5-ol 
• 159955-49-4 (E)-(4R,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-deca-2,9-dienoic acid methyl ester 
• 159955-44-9 (R)-5-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-hexyl]-dihydro-furan-2-one 
• 159955-46-1 (R)-5-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-hex-5-enyl]-dihydro-furan-2-one 
• 159955-43-8 (R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((R)-5-oxo-tetrahydro-furan-2-yl)-hexanal 
• 159955-40-5 ((1S,4S)-4-Benzyloxy-1-but-3-enyl-oct-7-enyloxy)-tert-butyl-dimethyl-silane 
• 159955-52-9 (E)-(4R,7R)-7-Hydroxy-4-(tetrahydro-pyran-2-yloxy)-deca-2,9-dienoic acid methyl ester 
• 159955-45-0 (R)-5-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-phenylsulfanyl-hexyl]-dihydro-furan-2-one 
• 159955-41-6 (4R,7R)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-decanedial 
• 159955-57-4 (3E,11E)-(5R,8S,13R,16S)-8,16-Diallyl-5,13-dihydroxy-1,9-dioxa-cyclohexadeca-3,11-diene-2,10-dione 
• 159955-51-8 (E)-(4R,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-4-(tetrahydro-pyran-2-yloxy)-deca-2,9-dienoic acid 

Downstream Products

• 146517-85-3 <2E,7E>-4,9-Dioxo-2,7-decadienoic acid 
• 146517-84-2 <2E,2'E,-7S,7'E>-4,9-dioxo-7-(4',9'-dioxo-2',7'-decadienoyloxy)-2-decenoic acid 
• 154869-41-7 <8S,16S>-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-2,5,10,13-tetraone 
• 156619-66-8 <8S,13RS,16S>-8,16-bis(2-oxopropyl)-13-hydroxy-1,9-dioxacyclohexadeca-2,5,10-trione 

Relevant articles and documents

Macrodiolide Diversification Reveals Broad Immunosuppressive Activity That Impairs the cGAS-STING Pathway

The development of new immunomodulatory agents can impact various areas of medicine. In particular, compounds with the ability to modulate innate immunological pathways hold significant unexplored potential. Herein, we report a modular synthetic approach to the macrodiolide natural product (?)-vermiculine, an agent previously shown to possess diverse biological effects, including cytotoxic and immunosuppressive activity. The synthesis allows for a high degree of flexibility in modifying the macrocyclic framework, including the formation of all possible stereoisomers. In total, 18 analogues were prepared. Two analogues with minor structural modifications showed clearly enhanced cancer cell line selectivity and reduced toxicity. Moreover, these compounds possessed broad inhibitory activity against innate immunological pathways in human PBMCs, including the DNA-sensing cGAS-STING pathway. Initial mechanistic characterization suggests a surprising impairment of the STING-TBK1 interaction.

Total Synthesis of (-)-Vermiculine

Macrodiolide (-)-vermiculine has been synthesized via intramolecular Mitsunobu reaction utilizing a C2 symmetrical diepoxide chiral synthon.

ALTERNATIVE SYNTHESIS OF (+/-)-VERMICULIN

The synthesis of (+/-)-vermiculin, 1, is reported.The key step is the condensation of the formyl ester 13 with the acetoacetic dianion to diester 15.