107389-91-3

Basic information

• Product Name: Cleroindicin B
• Synonyms: Cleroindicin B;4-Hydroxy-4-(2-hydroxyethyl)cyclohexanone
• CAS NO: 107389-91-3
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.19496
• Mol File: 107389-91-3.mol

Chemical Properties

• Boiling Point: 312.1 °C at 760 mmHg
• Flash Point: 156.8 °C
• Appearance: /
• Density: 1.185 g/cm³
• Vapor Pressure: 4.77E-05mmHg at 25°C
• Refractive Index: 1.513
• CAS DataBase Reference: Cleroindicin B(CAS DataBase Reference)
• NIST Chemistry Reference: Cleroindicin B(107389-91-3)
• EPA Substance Registry System: Cleroindicin B(107389-91-3)

Safety Data

• Hazardous Substances Data: 107389-91-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cleroindicin B is used as an anticancer agent for its potent activity against a broad spectrum of cancer cell lines. It functions by inducing apoptosis, a form of programmed cell death, thereby inhibiting the growth and proliferation of cancer cells.
Used in Drug Discovery and Development:
Cleroindicin B serves as an interesting target for research in drug discovery and development due to its unique structure and bioactivity. Its potential as a therapeutic agent for cancer treatment and other diseases is currently under investigation, with the aim of developing novel drugs that can effectively combat these conditions.
Used in Antimicrobial Applications:
Cleroindicin B is utilized as an antimicrobial agent, leveraging its inherent properties to combat microbial infections. Its effectiveness in this area contributes to the ongoing search for new antimicrobial compounds to address the growing issue of antibiotic resistance.
Used in Anti-inflammatory Applications:
Cleroindicin B is employed as an anti-inflammatory agent, capitalizing on its ability to reduce inflammation. This application is particularly relevant in the treatment of conditions where inflammation plays a significant role in disease progression, offering a potential therapeutic intervention for such scenarios.

InChI:InChI=1/C8H14O3/c9-6-5-8(11)3-1-7(10)2-4-8/h9,11H,1-6H2

Upstream product

• 189509-22-6 (8-hydroxy-1,4-dioxaspiro[4,5]dec-8-yl)-acetic acid ethyl ester 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 28251-63-0 tetraacetyl salidroside 
• 10338-51-9 Salidroside 
• 40661-45-8 cornoside 
• 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 
• 214678-47-4 Acetic acid (1R,4R)-1-(2-acetoxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl 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 
• 214678-38-3 ((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 
• 214678-48-5 Acetic acid (1R,4R)-1-(2-acetoxy-ethyl)-4-hydroxy-cyclohex-2-enyl ester 
• 214678-41-8 (1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(2-hydroxy-ethyl)-cyclohex-2-enol 

Downstream Products

• 189509-25-9 2-phenyl-1,3-dioxa-spiro[5.5]undecan-9-one 
• 123563-44-0 rengyoside B 
• 189509-27-1 acetic acid 2-phenyl-1,3-dioxa-spiro[5.5]undec-9-yl ester 
• 189577-42-2 acetic acid 2-phenyl-1,3-dioxa-spiro[5.5]undec-9-yl ester 
• 189509-26-0 2-phenyl-1,3-dioxa-spiro[5.5]undecan-9-ol 
• 189577-41-1 2-phenyl-1,3-dioxa-spiro[5.5]undecan-9-ol 
• 93675-85-5 cis-1-(2-hydroxyethyl)cyclohexane-1,4-diol 
• 101489-38-7 trans-1-(2-hydroxyethyl)cyclohexane-1,4-diol 
• 93675-96-8 rengyoxide dimethyl ketal 

Relevant articles and documents

Protection of the carbonyl group as 1,2,4-trioxane and its regeneration under basic conditions

(Chemical Equation Presented) An experimental protocol demonstrating the protection of the carbonyl group as 1,2,4-trioxane, the stability of the protecting group under a variety of reaction conditions, and the regeneration of the carbonyl group with Triton B in THF at room temperature is presented. The method provides a useful alternative for the protection of carbonyl compounds having acid-sensitive moieties.

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.