93675-85-5

Basic information

• Product Name: FORSYTHINOL
• Synonyms: Rengyol
• CAS NO: 93675-85-5
• Molecular Formula: C₈H₁₆O₃
• Molecular Weight: 160.21084
• Product Categories: Miscellaneous Natural Products
• Mol File: 93675-85-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: FORSYTHINOL(CAS DataBase Reference)
• NIST Chemistry Reference: FORSYTHINOL(93675-85-5)
• EPA Substance Registry System: FORSYTHINOL(93675-85-5)

Safety Data

• Hazardous Substances Data: 93675-85-5(Hazardous Substances Data)

Usage

Uses

Used in Antiviral Applications:
FORSYTHINOL is used as a broad-spectrum antiviral agent for its ability to inhibit the replication of various viruses, including influenza, herpes simplex, and human immunodeficiency virus (HIV). This makes it a promising candidate for the development of new antiviral medications.
Used in Anti-inflammatory Applications:
FORSYTHINOL is used as an anti-inflammatory agent for its demonstrated efficacy in reducing inflammation, which could be beneficial in the treatment of a range of inflammatory diseases.
Used in Antioxidant Applications:
FORSYTHINOL is used as an antioxidant agent to combat oxidative stress-related conditions due to its ability to neutralize harmful free radicals and protect cells from oxidative damage.

Upstream product

• 94414-03-6 4-[2-(acetyloxy)ethyl]-4-hydroxy-2,5-cyclohexadien-1-one 
• 93675-86-6 rengyoxide 
• 41043-88-3 4-acetoxycyclohexanone 
• 556-48-9 1,4-Cyclohexanediol 
• 58512-50-8 (4-hydroxycyclohexyl) acetate 
• 101489-37-6 (2R,3R,4S,5S,6R)-2-[2-(1-Hydroxy-4,4-dimethoxy-cyclohexyl)-ethoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 81053-18-1 2-(1-hydroxy-4-carbonylcyclohexyl) ethyl acetate 
• 214678-39-4 [(1R,4S,4aR,5R,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-yl]-acetic acid ethyl ester 
• 214678-36-1 ((1R,4S,4aR,5S,8aS)-5-Hydroxy-8-oxo-1,4,4a,5,8,8a-hexahydro-1,4-methano-naphthalen-5-yl)-acetic acid ethyl ester 
• 214678-40-7 (1R,4S,4aR,5R,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-5-(2-hydroxy-ethyl)-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-ol 
• 214678-37-2 ((1R,4S,4aR,5R,8aS)-5-Hydroxy-8-oxo-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-yl)-acetic acid ethyl ester 
• 214678-29-2 ((1R,4S,4aR,5S,8R,8aS)-5,8-Dihydroxy-1,4,4a,5,8,8a-hexahydro-1,4-methano-naphthalen-5-yl)-acetic acid ethyl ester 
• 214678-28-1 ((1S,4R,4aS,5R,8S,8aR)-5,8-Dihydroxy-1,4,4a,5,8,8a-hexahydro-1,4-methano-naphthalen-5-yl)-acetic acid ethyl ester 
• 214678-38-3 ((1R,4S,4aR,5R,8R,8aS)-5,8-Dihydroxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-yl)-acetic acid ethyl ester 

Downstream Products

• 93675-91-3 rengyol dibenzoate 
• 107389-92-4 4-hydroxy-4-(2'-acetoxyethyl)cyclohexanone 
• 93697-55-3 rengyoxide dimethyl ketal diacetate 
• 93675-92-4 rengyol triacetate 
• 93675-95-7 rengyoxide diacetate 
• 93675-96-8 rengyoxide dimethyl ketal 
• 93675-90-2 rengyol diacetate 

Relevant articles and documents

1,3-DIOL SYNTHESIS VIA CONTROLLED, RADICAL-MEDIATED C-H FUNCTIONALIZATION

The conversion of an alcohol into a 1,3- diol via controlled, radical-mediated C-H functionalization has been demonstrated. The method entails nearly quantitative conversion of an alcohol to the corresponding N-substitutedcarbamate, followed by a variant

1,3-Diol synthesis via controlled, radical-mediated C-H functionalization

The invention of a method for the synthesis of 1,3-diols from the corresponding alcohols is described, via controlled, radical-mediated C-H functionalization. The sequence described herein entails near quantitative conversion to the corresponding trifluoroethyl carbamate, followed by a variant of the Hofmann-Loffler-Freytag reaction, cyclization, and hydrolysis to provide the 1,3-diols. In addition to the 10 examples presented herein, the syntheses of four natural products are facilitated by this directed oxyfunctionalization. This methodology is demonstrated to be orthogonal to other known C-H oxidations. Finally, this sequence is efficient, practical, inexpensive, and scalable. Copyright

Chemo enzymatic synthesis of Rengyol and Isorengyol

Cyanohydrins 2 of O-protected 4-hydroxycyclohexanones 1 are excellent starting compounds for the synthesis of Isorengyol (I) and Rengyol (II). The cyano group of the O-benzyl derivative 2d is first converted into the corresponding aldehyde 4, which via Wi

A stereocontrolled route to cyclohexylethanoid natural products

Rengyol and seven related cyclohexylethanoid natural products have been synthesized in a stereocontrolled manner from a common starting material. In the present study the absolute configuration of the three chiral products has been determined and the first synthesis of a cyclohexylethanoid natural product bearing an oxetane ring has been accomplished.

Chemoenzymatic synthesis of rengyoside-A, -B, isorengyoside and synthesis of their aglycones

The chemoenzymatic synthesis of a group of naturally occurring cyclohexylethanoids, rengyoside-A, -B and isorengyoside, has been performed by enzymatic glucosidation of their chemically synthesized aglycones, rengyol, rengyoxide and isorengyol.

BIOGENESIS-LIKE TRANSFORMATION OF SALIDROSIDE TO RENGYOL AND ITS RELATED CYCLOHEXYLETANOIDS OF FORSYTHIA SUSPENSA

Photooxygenation of salidroside (8) in methanol in presence of Rose Bengal afforded cornoside (9), which, on high pressure hydrogenation with 5percent palladium on activated carbon, yielded rengyoside B (6).Reduction of 6 with sodium borohydride gave rengyoside A(5) stereoselectively.By enzymatic hydrolysis, 9, 6 and 5 furnished rengyolone (4), rengyoxide (3) and rengyol (1), respectively. Similerly, p-hydroxyphenylethanol (10), the aglycone part of salidroside (8), was oxygenated photochemically to a dienone alcohol, which cyclized spontaneously to rengyolone (4).Hallerone (17) was obtained by the photooxygenation of p-hydroxyphenylethyl acetate (10b).Thus the plausible biosynthetic routes from salidroside (8) to rengyol (1) and the related natural cyclohexylethanoids were simulated chemically.

STRUCTURES OF RENGYOSIDES A, B AND C, THREE GLUCOSIDES OF FORSYTHIA SUSPENSA FRUITS

Three new glucosides, rengyosides A, B and C, having as aglycones the reduced forms of phenylethanol, were isolated from Forsythia suspensa fruits.Chemical and spectroscopic studies established the structures of these natural products to be 2-(1,4-dihydroxycyclohexyl)ethyl β-D-glucopyranoside, 2-(1-hydroxy-4-ketocyclohexyl)ethyl β-D-glucopyranoside and 2-(1,4-dihydroxycyclohexyl)ethyl β-D-6-O-glucopyranoside, respectively.Saliroside, a possible biogenetic precursor of these glucosides, was also isolated. Key Word Index- Forsythia suspensa; Oleaceae; rengyoside A; rengyoside B; rengyoside C; cyclohexylethyl glucosides.

STEREOSTRUCTURE OF RENGYOL AND ISORENGYOL, PHENYLETHANOIDS OF FORSYTHIA SUSPENSA

Determination of the stereostructure of rengyol (1), a novel nonaromatic phenylethanoid natural product isolated from Forsythia suspensa, by synthetic means has been described.The Reformatsky reaction of 4-acetoxycyclohexanone with ethyl bromoacetate afforded two isomeric acetoxy esters (5, 6) and the one (5) which has an equatorial acetoxyl group yielded on LAH reduction a triol identified as rengyol (1).The isomer (7), obtained similarly from the other isomeric acetoxy ester (6), has also been isolated from the natural source and is named isorengyol.Further, dehydratation of the esters (5, 6) and subsequent pyrolytic deacetoxylation afforded a 1,3-cyclohaxadiene derivative (12), which on photosensitized cis-dioxygenation, followed by reduction, yielded rengyol (1) establishing its stereostructure to have 1,4-cis-cyclohexanediol system.These results supported the previous conclusion based on the 1H and 13C NMR spectral data.