5-acetyl-2,5-dimethyl-2-hydroxy-tetrahydrofuran-3-one..........Use of diacetyl dimer as an aromatic and/or flavouring substance

5-acetyl-2,5-dimethyl-2-hydroxy-tetrahydrofuran-3-one (diacetyl dimer of formula (I)) in the form of one of its stereoisomers or in the form of a mixture consisting of or containing two, three or four of its stereoisomers

SEE
http://www.google.com/patents/EP2028955B1?cl=en

The stereoisomers of diacetyl of formula (I) are:

ExamplesExample 1: Diacetyl dimer of formula (I)
• [0088]
  A racemic mixture of diacetyl dimer of formula (I) (comprising all 4 isomeres (Ia), (Ib), (Ic) and (Id)) which was prepared in accordance with the abovementioned instructions of Diels et al. in Chem. Ber. 1914, 47, 2355-2365and optionally purified according to the procedure described by Birch et al. in J. Chem. Soc. 1957, 412-414 was used in the following examples:
• [0089]
  Diacetyl (5 g) was mixed with water (20 g) and CaCO₃ (50 mg) was added. The mixture was stored in a stoppered vessel at 5 °C over night. The solution was acidified with diluted HCl and extracted with tert.-butylmethylether. The organic phases were washed with saturated sodium chloride solution, dried over Na₂SO₄ and the solvent and remaining diacetyl were evaporated in vacuo to yield 2.5 g diacetyl dimer of formula (I)._.
• [0090]
  According to the NMR the main isomer (80 % of all isomers) was the enantiomeric couple (Ia) and (Ib) (denoted *), the minor isomer (20 % of all isomers) the enantiomeric couple; (Ic) and (Id) (denoted **): ¹H-NMR (400 MHz, CDCl₃): δ = 3.37 (1H*, d, 19.1 Hz, H-4a), 2.94 (1H**, d, 19.1 Hz, H-4a), 2.6 (1H**, d, 19.1 Hz, H-4b), 2.34 (3H*, s, H-7), 2.29 (3H*, s, H-7), 2.25 (1H*, d, 19.0 Hz, H-4b), 1.61 (3H**, s, H-8 or 9), 1.52 (3H*, s, H-8 or 9), 1.51 (3H*, s, H-8 or 9), 1.48 (3H**, s, H-8 or 9) ppm.
  

  

  

  ¹³C-NMR (100 MHz, CDCl₃): δ = 210.8 (C, C-6), 208.5 (C, C-3), 98.7 (C, C-2), 84.1 (C, C-5), 40.9 (CH₂, C-4), 24.6 (CH₃, C-7), 24.2 (CH₃, C-9), 21.7 (CH₃, C-8) ppm.
• [0091]
  In the ¹³C-NMR spectra only the main isomer, the enantiomeric couple (Ia) and (Ib) was detected.

Example 1a: Characterization of diacetyl trimer (II)
• [0092]
  A racemic mixture which was prepared in accordance with the instructions of Poje and Perina in Tetrahedron 195, 41, 1985 - 1987 was used in the following examples. The mixture contained the following stereoisomers:
  

  

  MS (EI, 70 eV): m/z = 215 (6%), 155 (7%), 129 (16%), 111 (6%), 87 (13 %), 85 (14 %), 43 (100 %).
  ¹H-NMR (400 MHz, CDCl₃): δ = 4.67 (1H, bs, OH), 3.23 (1H, d, J = 13.6 Hz, H-6), 2.35 (3H, s, H-12), 2.25 (3H, s, H-9), 1.92 (1H, d, J = 13.6 Hz, H-6), 1.46 (3H, s, H-7), 1.40 (3H, s, H-10), 1.35 (3H, s, H-13) ppm.
  ¹³C-NMR (100 MHz, CDCl₃): δ = 210.42 (C, C-11), 208.05 (C, C-8), 114.49 (C, C6a), 112.50 (C, C-3a), 108.36 (C, C-2), 87.51 (C, C-5), 44.53 (CH₂, C-6), 25.10 (CH₃, C-9), 24.89 (CH₃, C-13), 24.87 (CH₃, C-12), 21.28 (CH₃, C-10), 20.90 (CH₃, C-7) ppm.

http://www.symrise.com/

 

germany food

SKATOLE スカトール

Name:	Skatole;3-Methylindole
Synonyms:	Skatole;3-Methylindole;1H-Indole, 3-methyl-;3-METHYLINDOLE;3-MI;3-Methyl-1H-indole;3-Methyl-4,5-benzopyrrole;83-34-1;AI3-24372;CCRIS 8961;EINECS 201-471-7;FEMA No. 3019;HSDB 3511;Indole, 3-methyl-;NSC 122024;Scatole;Skatol;beta-Methylindole;3-methyl-1H-indole;HMDB00466;;b-Methylindole;methyl-3-indole
Molecular Weight:	131.17446
Formula:	C9H9N
CAS:	83-34-1

1. 1D-1H:  NAME=expnmr_00539, EXPNO=1, PROCNO=1 ID [PPM] Intensity 1 7.590 11.105 2 7.574 12.000 3 7.334 10.482 4 7.319 13.010 5 7.201 6.126 6 7.185 11.592 7 7.171 7.532 8 7.135 8.993 9 7.119 12.705 10 7.105 5.835 11 6.947 15.242 12 2.333 100.501 2. 2D-[1H,1H]-TOCSY: 3. 1D-13C:  NAME=expnmr_00539, EXPNO=3, PROCNO=1 ID [PPM] Intensity 1 136.232 11.101 2 128.260 16.695 3 121.854 44.050 4 121.561 27.046 5 121.533 30.391 6 119.089 42.257 7 118.822 61.450 8 111.711 13.528 9 110.929 52.474 10 9.683 24.650 11 9.657 17.809 4. 1D-13C DEPT90:  NAME=expnmr_00539, EXPNO=4, PROCNO=1 ID [PPM] Intensity 1 121.844 1 2 121.542 1 3 119.09 1 4 118.808 1 5 110.916 1 5. 1D-13C DEPT135:  NAME=expnmr_00539, EXPNO=5, PROCNO=1 ID [PPM] Intensity 1 121.844 1 2 121.542 1 3 119.09 1 4 118.808 1 5 110.916 1 6 9.652 1 6. 2D-[1H,13C]-HSQC:  NAME=expnmr_00539, EXPNO=6, PROCNO=1 ID [PPM_1] [PPM_2] 1 7.186 121.477 2 6.944 121.212 3 7.579 118.565 4 7.115 118.548 5 7.325 110.554 6 2.333 9.575 7. 2D-[1H,13C]-HMBC:   8. 2D-[1H,1H]-COSY:

A novel synthetic methodology for preparation of thiocarbohydrazone by reacting thiocarbohydrazide with 1-acetyl-5-chloroisatin is described. The title compound was prepared by condensation of thiocarbohydrazide and substituted isatin in aqueous ethanol. The newly synthesized compound was characterized using 1H-NMR, 13C-NMR, FT-IR and mass spectrometry.

Molbank 2013, 2013(2), M798; doi:10.3390/M798

Short Note

N"-[(3Z)-1-Acetyl-5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene]thiocarbonohydrazide

Nataša Ristovska * , Frosa Anastasova and Marina Stefova

http://www.mdpi.com/1422-8599/2013/2/M798

Institute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss. Cyril and Methodius University, Gazi baba bb, 1000 Skopje, Macedonia

* Author to whom correspondence should be addressed.

 E-Mail: ristovska.natasha@on.net.mk;

Tel. +38-923-249-914; Fax +38-923-228-141.

Received: 8 February 2013; Accepted: 9 April 2013 / Published: 16 April 2013

N"-[(3Z)-1-Acetyl-5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene]thiocarbonohydrazide. A solution

of thiocarbohydrazide (0.53 g, 5 mmol) in 10 mL hot water was added in small aliquots to 1-acetyl-5-

chloroindoline-2,3-dione (1.12 g, 5 mmol) in 30 mL of ethanol. The mixture was refluxed for five

minutes and then was stirred overnight at room temperature. The resulting yellow precipitate was

collected by vacuum filtration, washed with ethanol/water solution (3:1, v/v) and air dried. Bright

yellow solid was obtained after recrystallization from ethanol in typical yield of 70%.

M.p.: 252–253 C

FTIR (KBr, cm−1): (NH) 3319, 3192, 3174, 3140, (CO) 1672, (CO) lactam 1605. 

1H-NMR (200 MHz, DMSO-d6): δ/ppm 14.15 (s, 1H, NH, C=N-NH-CS), 9.54 (s, 1H, NH CSNHNH2),

6.62 (s, 2H, CSNHNH2), 7.9–7.47 (m, 3H, Ar-H), 2.01 (s, 3H, CH3CO).

13C-NMR (200 MHz, DMSO-d6): /ppm 182.87 (C=S), 168.68 (C=O, NCOCH3), 148.64 (C=O,

lactam), 143.34 (C=N), 136.38 (CAr), 130.71 (CAr), 130.18 (CAr), 127.59 (CAr), 125.63 (CAr), 125.00

(CAr), 24.15 (NCOCH3).

MS m/z: [M−H]− at 310 (100%) represents the molecular ion with formula C11H10

35ClN5O2S (minusone H due to the negative ionization mode). The corresponding isotopic peak (for 37Cl) was observed at m/z 312 (26.1%).MS2 m/z: 236 (100%), 237 (7.5%), 238 (28.0%), 208 (1.5%), 194 (1%), 166 (1.5%).

MS3 m/z: 194 (91.1%), 195 (10.2%), 196 (20.5%), 166 (100%), 167 (11.7%), 168 (22.6%).

Anal. Calcd. for C11H10ClN5O2S (311.75): C, 42.38; H, 3.23; N, 22.46. Found: C, 42.22; H, 3.16; N, 22.25. 

Ss. Cyril and Methodius University in Skopje
Универзитет „Св. Кирил и Методиј“ во Скопје

http://www.ukim.edu.mk/

Statue of Ss. Cyril and Methodius in the center of the campus

The central building of the university

The student dormitory complex

SKOPJE

skopje..................ALL

http://newdrugapprovals.org/

PHENOBARBITAL

Profiles of Drug Substances, Excipients and Related ...

https://books.google.co.in/books?isbn=0080861024

Klaus Florey - 1978 - ‎Science

Mesley and Clements7 evaluated the infrared identification of phenobarbital with particular ... 3 Nuclear Magnetic Resonance Spectral Assignments for PhenobarbitalChemical Shift ... The NMR spectrum9 of phenobarbital in DMSO at 90 Meg  ..

SEE

http://www.swgdrug.org/Monographs/PHENOBARBITAL.pdf









SEE

http://pubs.acs.org/doi/abs/10.1021/jp409201v

Metal complex will help alleviate bottleneck in asymmetric catalyst screening

SEE
http://www.rsc.org/chemistryworld/2013/07/stereochemical-analysis-asymmetric-catalysis

Simple method for identifying incorrect structures of organic molecules due to NMR misassignments

Simple method for identifying incorrect structures of organic molecules due to NMR misassignments



SEE
http://www.rsc.org/chemistryworld/2013/06/nmr-misassignments-spreadsheet-artificial-neural-networks

Phenolphthalein 酚酞

IH NMR














13C NMR






MASS




RAMAN









http://www.intechopen.com/books/an-integrated-view-of-the-molecular-recognition-and-toxinology-from-analytical-procedures-to-biomedical-applications/cyclodextrin-based-spectral-changes