1615-99-2

Basic information

• Product Name: FERN-9(11)-ENE
• Synonyms: FERN-9(11)-ENE;Fern-9(11)ene solution;d:c-friedo-b':a'-neogammacer-9(11)-ene;Davallen;Davallene;Fernen
• CAS NO: 1615-99-2
• Molecular Formula: C₃₀H₅₀
• Molecular Weight: 410.72
• Mol File: 1615-99-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 170-171 °C
• Boiling Point: 463.7°Cat760mmHg
• Flash Point: 233.6°C
• Appearance: /
• Density: 0.96g/cm³
• Vapor Pressure: 2.47E-08mmHg at 25°C
• Refractive Index: 1.527
• Storage Temp.: 2-8°C
• CAS DataBase Reference: FERN-9(11)-ENE(CAS DataBase Reference)
• NIST Chemistry Reference: FERN-9(11)-ENE(1615-99-2)
• EPA Substance Registry System: FERN-9(11)-ENE(1615-99-2)

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: 1615-99-2(Hazardous Substances Data)

Usage

Description

FERN-9(11)-ENE is a natural organic compound belonging to the class of diterpenes, which are hydrocarbons derived from the combination of two isoprene units. It is found in a variety of plants, including ferns, and is known for its potential biological activities such as anti-inflammatory, anti-fungal, and anti-cancer properties. Its chemical structure consists of a fused four-ring system with a characteristic double bond at the 9(11) position, giving it its unique and important chemical properties.
Used in Pharmaceutical Industry:
FERN-9(11)-ENE is used as a pharmaceutical agent for its potential anti-inflammatory, anti-fungal, and anti-cancer properties. Its biological activities make it a promising candidate for the development of new drugs to treat various diseases.
Used in Flavor and Fragrance Industry:
FERN-9(11)-ENE is used as a flavoring agent in food products due to its unique chemical properties. Its characteristic double bond at the 9(11) position contributes to its distinct aroma and flavor, making it a valuable ingredient in the creation of food products with specific taste profiles.

InChI:InChI=1/C30H50/c1-20(2)21-10-13-25-28(21,6)18-19-29(7)23-11-12-24-26(3,4)15-9-16-27(24,5)22(23)14-17-30(25,29)8/h14,20-21,23-25H,9-13,15-19H2,1-8H3/t21-,23+,24+,25-,27-,28-,29-,30+/m1/s1

Synthetic route

fern-9(11)-ene-3,12-dione (53527-39-2) → fern-9(11)-ene (1615-99-2)

Conditions	Yield
With potassium hydroxide; hydrazine In diethylene glycol Heating;

fern-9(11)-en-25-ol mesylate (160803-78-1) → fern-9(11)-ene (1615-99-2) + 9,25-cyclofernane

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 10h; Heating; Yields of byproduct given;
With lithium aluminium tetrahydride In tetrahydrofuran for 10h; Heating; Yield given;

Fem-9(11)-en-20-on → fern-9(11)-ene (1615-99-2)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate In diethylene glycol

fern-9(11)-en-25-oic acid (138935-87-2) → fern-9(11)-ene (1615-99-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 60 percent / LiAlH4 / tetrahydrofuran / 5 h / Heating 2: pyridine / 0.5 h / 0 °C 3: LiAlH4 / tetrahydrofuran / 10 h / Heating View Scheme

((3R,3aR,5aR,5bR,7aS,11aR,13aS,13bR)-3-Isopropyl-3a,5a,8,8,13a-pentamethyl-2,3,3a,4,5,5b,6,7,7a,8,9,10,11,13,13a,13b-hexadecahydro-1H,5aH-cyclopenta[a]chrysen-11a-yl)-methanol (160803-79-2) → fern-9(11)-ene (1615-99-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 0.5 h / 0 °C 2: LiAlH4 / tetrahydrofuran / 10 h / Heating View Scheme

fern-9(11)-ene-3β,12α-diol (53527-35-8) → fern-9(11)-ene (1615-99-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: CrO3, aq. H2SO4 2: N2H4, KOH / bis-(2-hydroxy-ethyl) ether / Heating View Scheme

fern-9(11)-ene (1615-99-2) → fern-9(11)-ene-12-one (58207-92-4)

Conditions	Yield
With chromium(VI) oxide; acetic acid

fern-9(11)-ene (1615-99-2) → 12α-hydroxyfern-9(11)-ene

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. CrO3; AcOH 2: 20 mg / Na; n-PrOH / 1 h View Scheme

Upstream product

• 546-99-6 hop-17⁽²¹⁾-ene 
• 53527-39-2 fern-9⁽¹¹⁾-ene-3,12-dione 
• 160803-78-1 fern-9⁽¹¹⁾-en-25-ol mesylate 
• 138935-87-2 fern-9⁽¹¹⁾-en-25-oic acid 
• 160803-79-2 ((3R,3aR,5aR,5bR,7aS,11aR,13aS,13bR)-3-Isopropyl-3a,5a,8,8,13a-pentamethyl-2,3,3a,4,5,5b,6,7,7a,8,9,10,11,13,13a,13b-hexadecahydro-1H,5aH-cyclopenta[a]chrysen-11a-yl)-methanol 
• 53527-35-8 fern-9(11)-ene-3β,12α-diol 
• 6090-29-5 (3R,3aS,5aS,5bS,7aR,11aS,13aR,13bS)-3-Isopropyl-3a,5a,8,8,11a,13a-hexamethyl-1,2,3,3a,4,5,5a,5b,6,7,7a,8,10,11,11a,13,13a,13b-octadecahydro-cyclopenta[a]chrysen-9-one 
• 90582-44-8 sorghumol 
• 2472-29-9 filic-3-ene 
• 1615-99-2 fern-9⁽¹¹⁾-ene 
• 1750-35-2 fern-8-ene 
• 1615-98-1 9βH-fern-7-ene 
• 1615-98-1 fern-7-ene 
• 1615-95-8 adian-5-ene 

Downstream Products

• 2318-80-1 Ferna-7,9(11)-diene 
• 58207-92-4 Fern-9⁽¹¹⁾-en-12-one 
• 69753-81-7 9β,11β-Epoxyfernane 
• 69753-81-7 9α,11α-Epoxyfernane 
• 2318-80-1 ferna-7,9(11)-diene 
• 21681-17-4 neohop-13⁽¹⁸⁾-ene 
• 546-99-6 hop-17⁽²¹⁾-ene 
• 1615-99-2 8Η-fern-9(11)-ene 
• 1750-35-2 fern-8-ene 
• 1615-98-1 9βH-fern-7-ene 

Relevant articles and documents

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Spiro-triterpenes from clay-catalysed rearrangement of hopenes: NMR structural elucidation and occurrence in a recent sediment

Acidic K-10 montmorillonite clay-catalysed rearrangement of hop-22(29)-ene 5 and of hop-17(21)-ene 6 leads to the formation of small quantities of various fernenes and of new compounds, the 14-methyl-13,15-cyclo-B':A'-neo-26-nor-14,15-seco-18α-gammacer-7-ene 8 and its Δ8- and Δ9((11))-isomers 9 and 10, the structures of which have been established by MS and NMR spectroscopy. This novel hopane skeleton transposition also operates on bacterial sedimentary hopenes, as shown by GC-MS investigations of the alkene fraction from a recent lacustrine sediment.

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