124649-26-9

Basic information

• Product Name: tuberonic acid
• Synonyms: tuberonic acid;(1R)-2α-[(Z)-5-Hydroxy-2-pentenyl]-3-oxocyclopentane-1α-acetic acid;(1R,2S)-2-[(Z)-5-Hydroxy-2-pentenyl]-3-oxocyclopentane-1-acetic acid;(1R,2S)-Tuberonic acid;2-[(1R)-3-Oxo-2α-[(2Z)-5-hydroxy-2-pentenyl]cyclopentan-1α-yl]acetic acid;TUBERONIC ACID(P)
• CAS NO: 124649-26-9
• Molecular Formula: C12H18 O4
• Molecular Weight: 226.27
• Mol File: 124649-26-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 429.5°C at 760 mmHg
• Flash Point: 227.7°C
• Appearance: /
• Density: 1.156g/cm³
• Vapor Pressure: 3.52E-09mmHg at 25°C
• Refractive Index: 1.514
• CAS DataBase Reference: tuberonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: tuberonic acid(124649-26-9)
• EPA Substance Registry System: tuberonic acid(124649-26-9)

Safety Data

• Hazardous Substances Data: 124649-26-9(Hazardous Substances Data)

Usage

Uses

(+)-Tuberonic Acid has shown to have tuber-inducting properties. (+)-Tuberonic Acid is an analogue of Jasmonic Acid (J210520), a major constituent of essential oil of Jasmine. Used by the fragrance industry

InChI:InChI=1/C12H18O4/c13-7-3-1-2-4-10-9(8-12(15)16)5-6-11(10)14/h1-2,9-10,13H,3-8H2,(H,15,16)/b2-1-/t9-,10+/m1/s1

Upstream product

• 932391-42-9 2-((1R,2S)-3-oxo-2-((Z)-5-(tetrahydro-2H-pyran-2-yloxy)-pent-2-enyl)cyclopentyl)ethanoic acid 
• 68931-47-5 [(1S,2S)-2-(5-Hydroxy-pent-2-ynyl)-3-oxo-cyclopentyl]-thioacetic acid S-tert-butyl ester 
• 81760-96-5 2,5-diethoxycarbonyl-3-methoxycarbonylmethyl-2-(5-tetrahydropyranyloxy-2-pentynyl)cyclopentanone 
• 81760-94-3 diethyl 2-(tetrahydropyranyloxy-2-pentynyl)-3-oxopentanedioate 
• 85604-61-1 2-allyl-2,5-diethoxycarbonyl-4-methoxycarbonylmethylcyclopentanone 
• 51557-87-0 trans-2-allyl-1-cyclopentanone-3-acetic acid methyl ester 
• 92775-68-3 1-methanesulfonyloxy-5-(tetrahydro-2-pyranyloxy)pent-2-yne 
• 51442-80-9 5-(tetrahydro-2H-pyran-2-yloxy)-2-pentyn-1-ol 
• 81761-06-0 methyl (1S*,2S*)-2-[(2Z)-5-hydroxy-2-pentenyl]-3-oxocyclopentaneacetate 
• 68931-53-3 5'-Hydroxythiojasmonsaeure-S-t-butylester 

Downstream Products

• 140631-27-2 [(1R,2R,2'Z)-2-(5'-hydroxypent-2'-enyl)-3-oxocyclopentane]acetic acid 
• 68931-43-1 (Z)-1,2-trans-8,13-dioxo-7-oxabicyclo<8.3.0>tridec-3-ene 

Relevant articles and documents

First total synthesis of tuberonic acid

A vinyl group as an acetic acid side chain was attached to the optically active monoacetate of 4-cyclopentene-1,3-diol with CH2{double bond, long}CHMgBr, LiCl, and a CuCN catalyst to produce the SN2-type product, from which the full carbon skeleton of tuberonic acid was constructed through Mitsunobu inversion, Claisen rearrangement, and Wittig reaction. At the last stage, the THP protective group was removed with MgBr2 in Et2O. The diastereomeric ratio of tuberonic acid and the trans isomer was 92:8 by 1H NMR spectroscopy.

Synthesis of Jasmine Ketolactone

The synthesis of jasmine ketolactone 3, a minor component of Italian jasmine oil, via the intramolecular Michael reaction is described.