1615-92-5

Basic information

• Product Name: HOP-21(22)-ENE
• Synonyms: HOP-21(22)-ENE;Hop-21(22)-ene solution;Hop-21(22)-ene (17β(H))
• CAS NO: 1615-92-5
• Molecular Formula: C₃₀H₅₀
• Molecular Weight: 410.72
• Mol File: 1615-92-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 460.703°C at 760 mmHg
• Flash Point: 232.134°C
• Appearance: /
• Density: 0.942g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.51
• Storage Temp.: −20°C
• CAS DataBase Reference: HOP-21(22)-ENE(CAS DataBase Reference)
• NIST Chemistry Reference: HOP-21(22)-ENE(1615-92-5)
• EPA Substance Registry System: HOP-21(22)-ENE(1615-92-5)

Safety Data

• Hazard Codes: F,Xn,N
• Statements: 11-38-50/53-65-67
• Safety Statements: 60-61-62
• RIDADR: UN 1262 3/PG 2
• WGK Germany: 1
• F: 10-23
• Hazardous Substances Data: 1615-92-5(Hazardous Substances Data)

Usage

General Description

Hop-21-ene is a versatile compound with applications in chemistry and the fragrance industry, and it plays a key role in the sensory characteristics of hops used in brewing. It is a colorless to yellow oily liquid with a pungent odor. Hop-21-ene is insoluble in water but soluble in organic solvents such as ether, alcohol, and benzene.

InChI:InChI=1/C30H50/c1-20(2)21-12-17-27(5)22(21)13-18-29(7)24(27)10-11-25-28(6)16-9-15-26(3,4)23(28)14-19-30(25,29)8/h22-25H,9-19H2,1-8H3/t22-,23-,24+,25+,27-,28-,29+,30+/m0/s1

Upstream product

• 1721-59-1 hydroxyisohopane 
• 111-02-4 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene 
• 1721-59-1 hopan-22-ol 

Downstream Products

• 1172-78-7 17αH-trisnorhopanone 
• 1172-78-7 trisnorhopanone 
• 1172-78-7 22,29,30-trinor(17αH)-hopan-21-one 
• 10379-52-9 trisnor(17α)hopan-21-one 

Relevant articles and documents

Alicyclobacillus acidocaldarius Squalene-Hopene Cyclase: The Critical Role of Steric Bulk at Ala306 and the First Enzymatic Synthesis of Epoxydammarane from 2,3-Oxidosqualene

The acyclic molecule squalene (1) is cyclized into 6,6,6,6,5-fused pentacyclic hopene (2) and hopanol (3; ca. 5:1) through the action of Alicyclobacillus acidocaldarius squalene-hopene cyclase (AaSHC). The polycyclization reaction proceeds with regio- and stereochemical specificity under precise enzymatic control. This pentacyclic hopane skeleton is generated by folding 1 into an all-chair conformation. The Ala306 residue in AaSHC is conserved in known squalene-hopene cyclases (SHCs); however, increasing the steric bulk (A306T and A306V) led to the accumulation of 6,6,6,5-fused tetracyclic scaffolds possessing 20R stereochemistry in high yield (94 % for A306V). The production of the 20R configuration indicated that 1 had been folded in a chair-chair-chair-boat conformation; in contrast, the normal chair-chair-chair-chair conformation affords the tetracycle with 20S stereochemistry, but the yield produced by the A306V mutant was very low (6 %). Consequently, bulk at position 306 significantly affects the stereochemical fate during the polycyclization reaction. The SHC also accepts (3R) and (3S)-2,3-oxidosqualenes (OXSQs) to generate 3α,β-hydroxyhopenes and 3α,β-hydroxyhopanols through polycyclization initiated at the epoxide ring. However, the Val and Thr mutants generated epoxydammarane scaffolds from (3R)-OXSQ; this indicated that the polycyclization cascade started in these instances at the terminal double bond position. This work is the first to report the polycyclization of oxidosqualene starting at the terminal double bond.

Fern constituents: Two new triterpenoid hydrocarbons, hop-16-ene and isohop-22(29)-ene, isolated from Davallia mariesii

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