96405-62-8

Basic information

• Product Name: goniotriol
• Synonyms: goniotriol;(+)-6-(1,2-Dihydroxy-2-phenylethyl)-5,6-dihydro-5-hydroxy-2H-pyran-2-one;(7R)-2,3-Dideoxy-7-C-phenyl-D-xylohept-2-enonic acid delta-lactone
• CAS NO: 96405-62-8
• Molecular Formula: C₁₃H₁₄O₅
• Molecular Weight: 250.25
• Mol File: 96405-62-8.mol

Chemical Properties

• Boiling Point: 554.8°Cat760mmHg
• Flash Point: 218°C
• Appearance: /
• Density: 1.419g/cm³
• Vapor Pressure: 3.81E-13mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: goniotriol(CAS DataBase Reference)
• NIST Chemistry Reference: goniotriol(96405-62-8)
• EPA Substance Registry System: goniotriol(96405-62-8)

Safety Data

• Hazardous Substances Data: 96405-62-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Goniotriol is used as a pharmaceutical agent for its potential therapeutic effects. The bioactive properties of goniotriol make it a promising candidate for the development of new drugs and treatments.
Used in Cosmetic Industry:
Goniotriol is used as an ingredient in cosmetic products for its potential skin benefits. Its unique chemical structure may contribute to improved skin health and appearance.
Used in Food Industry:
Goniotriol is used as a natural additive in the food industry for its potential health benefits. Its presence in food products may provide consumers with added nutritional value.
Used in Agricultural Industry:
Goniotriol is used as a natural pesticide or fertilizer in the agricultural industry. Its bioactive properties may help protect crops from pests and promote plant growth.

InChI:InChI=1/C13H14O5/c14-9-6-7-10(15)18-13(9)12(17)11(16)8-4-2-1-3-5-8/h1-7,9,11-14,16-17H/t9-,11+,12+,13+/m0/s1

Upstream product

• 944353-10-0 (5S,6R)-6-((1R,2R)-1,2-bis(methoxymethoxy)-2-phenylethyl)-5-(benzyloxy)-5,6-dihydropyran-2-one 
• 100-58-3 phenylmagnesium bromide 
• 1054649-03-4 C₂₀H₂₀O₅ 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 162466-15-1 (2S,3R)-2,3-isopropylidenyloxy-3-phenylpropanyl tert-butyldiphenylsilyl ether 
• 162466-13-9 (2S,3R)-2-hydroxy-3-acetoxyl-3-phenylpropanyl tert-butyldiphenylsilyl ether 
• 162466-14-0 (2S,3R)-2,3-dihydroxy-3-phenylpropanyl tert-butyldiphenylsilyl ether 
• 162600-01-3 (1S,2R,3R)-1-(2-furyl)-2,3-isopropylidenyloxy-3-phenyl-1-propanol 

Downstream Products

• 136778-39-7 (+)-goniofufurone 

Relevant articles and documents

Synthesis of (+)-goniopypyrone and (+)-goniotriol using Pd-catalyzed carbonylation

Syntheses of (+)-goniopypyrone and (+)-goniotriol isolated from Goniothalamus giganteus were achieved. The key steps involve Pd-catalyzed carbonylation for lactone ring formation and diastereoselective reduction of ynone using the (R)-CBS catalyst and borane dimethyl sulfide complex.

Stereoselective synthesis of (+)-goniodiol, (+)-goniotriol, (-)-goniofupyrone, and (+)-altholactone using a catalytic asymmetric hetero-Diels-Alder/allylboration approach

The stereoselective total synthesis of several members of the styryllactone family was achieved efficiently from common intermediate 8, prepared by a catalytic asymmetric inverse-electron-demand hetero-Diels-Alder/allylboration sequence. The transformatio

Stereoselective total synthesis of bioactive styryllactones (+)-goniofufurone, (+)7-epi-goniofufurone, (+)-goniopypyrone, (+)-goniotriol, (+)-altholactone, and (-)etharvensin

(Chemical Equation Presented) Stereoselective total synthesis of biologically active styryllactones 7-epi-goniofufurone, goniofufurone, goniopypyrone, goniotriol, altholactone, and etharvensin was achieved in high overall yields from a common intermediate

Stereocontrolled syntheses of novel styryl lactones, (+)-goniodiol, (+)- goniotriol, (+)-8-acetylgoniotriol, (+)-goniofufurone, (+)-9- deoxygoniopypyrone, (+)-goniopypyrone, and (+)-altholactone from common intermediates and cytotoxicity of their congener

Concise syntheses of (+)-goniodiol, (+)-goniotriol, (+)-8- acetylgoniotriol, (+)-goniofufurone, (+)-9-deoxygoniopypyrone, (+)- goniopypyrone, and (+)-altholactone and their congeners from chiral lactonic aldehydes 27 and 36 as common intermediates are des

Total synthesis of antitumor Goniothalamus styryllactones

Synthesis of eight enantiopure styryllactones has been achieved from a common precursor: ethyl (2S, 3S, 4R)-4-(t-butyldimethylsilyloxy)-2,3- isopropylidenedioxy-4-phenylbutanoate 16, prepared in five steps and 65% yield from (R)-mandelic acid. Key elements for the synthesis of goniofufurone 3, goniopypyrone 4, goniobutenolides A and B (5, 6) and 7-epi-goniofufurone 7 were the introduction of the Z-acrylate moiety by a Julia coupling between 16 or its epimer in benzylic position and methyl 3-phenylsulfonyl orthopropionate 11 followed by a highly diastereoselective reduction of the resulting β-keto sulfone which sets up the last of the four contiguous asymmetric center. In the case of styryllactones 4 and 7, prior to the Julia coupling, the benzyl sterocenter of 16 was efficiently inverted by a Mitsunobu reaction. Goniodiol 1 and 9-deoxygoniopypyrone 2 were synthesized via an efficient coupling between the primary triflate derived from the common intermediate 16 or its epimer and Ghosez's sulfone 11 followed by lactonization and PhSO2H elimination. Goniodiol 1 has been efficiently converted to another styryllactone: isogoniothalamin epoxide 41. Addition of the Ghosez's sulfone to an epoxide derived from the enantiomer of 16 allowed a short synthesis of 8-epi-9-deoxygoniopypyrone 8, thereby establishing that its structure is the following: (1R, 5R, 7S, 8S)-8-hydroxy-7-phenyl-2,6- dioxabicyclo[3.3.1] nonan-3-one.

Stereoselective Syntheses of (+)-Goniotriol, (+)-8-Acetylgoniotriol, (+)-Goniodiol, (+)-9-Deoxygoniopypyrone, (+)-Altholactone, and (-)-Goniofupyrone

The γ-lactone intermediate (-)-7, derived from (+)-tricarbonyl(η6-o-(trimethylsilyl)benzaldehyde)chromium(0) complex, was efficiently converted into the corresponding δ-lactone intermediate (-)-11. This second intermediate has been shown to be a versatile compound for stereoselective syntheses of natural styryllactones possessing a six-membered lactone moiety, isolated from Goniothalamus giganteus, by transforming it into (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniodiol, (+)-9-deoxygoniopypyrone, (+)-altholactone, and (-)-goniofupyrone.

Enantiospecific Syntheses of (+)-Goniofufurone, (+)-7-epi-Goniofufurone, (+)-Goniobutenolide A, (-)-Goniobutenolide B, (+)-Goniopypyrone, (+)-Altholactone, (+)-Goniotriol, and (+)-7-Acetylgoniotriol

Practical and efficient syntheses of a number of styryl lactones with various structural complexities were accomplished from commercially available and inexpensive D-glycero-D-gulo-heptono-γ-lactone (D-glucoheptonic γ-lactone) (11).Lactone 11 was converte

Asymmetric Total Synthesis of (+)-Goniotriol and (+)-Goniofufurone

Thr Enantioselective synthesis of two antitumor styryl lactones, (+)-goniotriol and (+)-goniofufurone, have been completed starting from cinnamyl alcohol in ten and eleven steps with an overall yield of 21percent and 12percent, respectively.