21681-17-4

Basic information

• Product Name: NEOHOP-13(18)-ENE
• Synonyms: NEOHOP-13(18)-ENE;Neohop-13(18)ene solution;b':a'-neogammacer-13(18)-ene;(17R)-17-Methyl-28-nor-5α-hopa-13(18)-ene;B':A'-Neo-5α-gammacer-13(18)-ene;Hopene II;Wallichiene
• CAS NO: 21681-17-4
• Molecular Formula: C₃₀H₅₀
• Molecular Weight: 410.72
• Mol File: 21681-17-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 196-197 °C
• Boiling Point: 464.2±12.0 °C(Predicted)
• Appearance: /
• Density: 0.97±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: NEOHOP-13(18)-ENE(CAS DataBase Reference)
• NIST Chemistry Reference: NEOHOP-13(18)-ENE(21681-17-4)
• EPA Substance Registry System: NEOHOP-13(18)-ENE(21681-17-4)

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: 21681-17-4(Hazardous Substances Data)

Upstream product

• 111-02-4 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene 
• 1615-99-2 fern-9⁽¹¹⁾-ene 
• 2472-29-9 filic-3-ene 
• 546-99-6 hop-17⁽²¹⁾-ene 
• 1750-35-2 fern-8-ene 

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.

Acid-Induced Rearrangement of Triterpenoid Hydrocarbons Belonging to the Hopane and Migrated Hopane Series

The acid-catalyzed rearrangement of triterpenoid monoenes belonging to the hopane and migrated hopane series with sulfuric acid and boron trifluoride etherate was investigated.By selecting the reaction conditions, a variety of the monoenes of these series, including three new compounds, 9βH-fern-7-ene (3c), 8βH-fern-9(11)-ene (4b), and adian-5(10)-ene (5b), were obtained.For comparison, oleanenes and migrated oleanenes were also subjected to the same reaction.Keywords--acid-induced rearrangement; triterpenoid hydrocarbon; hopane, migrated hopane; 9βH-fern-7-ene; 8βH-fern-9(11)-ene; adian-5(10)-ene; sulfuric acid; boron trifluoride