Extraction, purification, and spectroscopic characterization of a mixture of capsaicinoids

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

This laboratory experiment provides a safe and effective way to instruct undergraduate organic chemistry students about natural-product extraction, purification, and NMR spectroscopic characterization. On the first day, students extract dried habañero peppers with toluene, perform a pipet silica gel column to separate carotenoids from capsaicinoids, and perform thin-layer chromatography. On the second day, students characterize their mixture of capsaicinoids, approximating the relative quantities of the two primary capsaicinoids, capsaicin and dihydrocapsaicin, by NMR. Additionally, students are introduced to 2D NMR analysis. The effectiveness of the laboratory is assessed by two methods: a qualitative postlab student self-assessment and a quantitative pre- and postlab test. For the qualitative assessment, students stated that they acquired an improved understanding of NMR from the experiment. Accordingly, the total average on the quantitative prelab and postlab 8-point test increased from 3.43 ± 1.62 (SD) to 4.25 ± 1.48 (SD) and demonstrated a statistically significant improvement (p value of 0.001), as did the average for the 5-points of NMR-related questions in the prelab- and postlab 8-point test: 1.61 ± 1.21 (SD) to 2.13 ± 1.11 (SD), with p value of 0.004.

Original languageEnglish (US)
Pages (from-to)1574-1579
Number of pages6
JournalJournal of Chemical Education
Volume88
Issue number11
DOIs
StatePublished - Nov 1 2011

Fingerprint

Purification
Students
Nuclear magnetic resonance
student
Thin layer chromatography
Capsaicin
Silica Gel
Toluene
Carotenoids
laboratory experiment
self-assessment
Biological Products
chemistry
Experiments
experiment

Keywords

  • Analytical Chemistry
  • Chromatography
  • Hands-On Learning/ Manipulatives
  • IR Spectroscopy
  • Laboratory Instruction Organic Chemistry
  • Natural Products
  • NMR Spectroscopy
  • Second-Year Undergraduate
  • Upper-Division Undergraduate

ASJC Scopus subject areas

  • Chemistry(all)
  • Education

Cite this

@article{dc594037b18045e89d50255d0b297b27,
title = "Extraction, purification, and spectroscopic characterization of a mixture of capsaicinoids",
abstract = "This laboratory experiment provides a safe and effective way to instruct undergraduate organic chemistry students about natural-product extraction, purification, and NMR spectroscopic characterization. On the first day, students extract dried haba{\~n}ero peppers with toluene, perform a pipet silica gel column to separate carotenoids from capsaicinoids, and perform thin-layer chromatography. On the second day, students characterize their mixture of capsaicinoids, approximating the relative quantities of the two primary capsaicinoids, capsaicin and dihydrocapsaicin, by NMR. Additionally, students are introduced to 2D NMR analysis. The effectiveness of the laboratory is assessed by two methods: a qualitative postlab student self-assessment and a quantitative pre- and postlab test. For the qualitative assessment, students stated that they acquired an improved understanding of NMR from the experiment. Accordingly, the total average on the quantitative prelab and postlab 8-point test increased from 3.43 ± 1.62 (SD) to 4.25 ± 1.48 (SD) and demonstrated a statistically significant improvement (p value of 0.001), as did the average for the 5-points of NMR-related questions in the prelab- and postlab 8-point test: 1.61 ± 1.21 (SD) to 2.13 ± 1.11 (SD), with p value of 0.004.",
keywords = "Analytical Chemistry, Chromatography, Hands-On Learning/ Manipulatives, IR Spectroscopy, Laboratory Instruction Organic Chemistry, Natural Products, NMR Spectroscopy, Second-Year Undergraduate, Upper-Division Undergraduate",
author = "Carl Wagner and Thomas Cahill and Pamela Marshall",
year = "2011",
month = "11",
day = "1",
doi = "10.1021/ed1006025",
language = "English (US)",
volume = "88",
pages = "1574--1579",
journal = "Journal of Chemical Education",
issn = "0021-9584",
publisher = "American Chemical Society",
number = "11",

}

TY - JOUR

T1 - Extraction, purification, and spectroscopic characterization of a mixture of capsaicinoids

AU - Wagner, Carl

AU - Cahill, Thomas

AU - Marshall, Pamela

PY - 2011/11/1

Y1 - 2011/11/1

N2 - This laboratory experiment provides a safe and effective way to instruct undergraduate organic chemistry students about natural-product extraction, purification, and NMR spectroscopic characterization. On the first day, students extract dried habañero peppers with toluene, perform a pipet silica gel column to separate carotenoids from capsaicinoids, and perform thin-layer chromatography. On the second day, students characterize their mixture of capsaicinoids, approximating the relative quantities of the two primary capsaicinoids, capsaicin and dihydrocapsaicin, by NMR. Additionally, students are introduced to 2D NMR analysis. The effectiveness of the laboratory is assessed by two methods: a qualitative postlab student self-assessment and a quantitative pre- and postlab test. For the qualitative assessment, students stated that they acquired an improved understanding of NMR from the experiment. Accordingly, the total average on the quantitative prelab and postlab 8-point test increased from 3.43 ± 1.62 (SD) to 4.25 ± 1.48 (SD) and demonstrated a statistically significant improvement (p value of 0.001), as did the average for the 5-points of NMR-related questions in the prelab- and postlab 8-point test: 1.61 ± 1.21 (SD) to 2.13 ± 1.11 (SD), with p value of 0.004.

AB - This laboratory experiment provides a safe and effective way to instruct undergraduate organic chemistry students about natural-product extraction, purification, and NMR spectroscopic characterization. On the first day, students extract dried habañero peppers with toluene, perform a pipet silica gel column to separate carotenoids from capsaicinoids, and perform thin-layer chromatography. On the second day, students characterize their mixture of capsaicinoids, approximating the relative quantities of the two primary capsaicinoids, capsaicin and dihydrocapsaicin, by NMR. Additionally, students are introduced to 2D NMR analysis. The effectiveness of the laboratory is assessed by two methods: a qualitative postlab student self-assessment and a quantitative pre- and postlab test. For the qualitative assessment, students stated that they acquired an improved understanding of NMR from the experiment. Accordingly, the total average on the quantitative prelab and postlab 8-point test increased from 3.43 ± 1.62 (SD) to 4.25 ± 1.48 (SD) and demonstrated a statistically significant improvement (p value of 0.001), as did the average for the 5-points of NMR-related questions in the prelab- and postlab 8-point test: 1.61 ± 1.21 (SD) to 2.13 ± 1.11 (SD), with p value of 0.004.

KW - Analytical Chemistry

KW - Chromatography

KW - Hands-On Learning/ Manipulatives

KW - IR Spectroscopy

KW - Laboratory Instruction Organic Chemistry

KW - Natural Products

KW - NMR Spectroscopy

KW - Second-Year Undergraduate

KW - Upper-Division Undergraduate

UR - http://www.scopus.com/inward/record.url?scp=80054002556&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80054002556&partnerID=8YFLogxK

U2 - 10.1021/ed1006025

DO - 10.1021/ed1006025

M3 - Article

VL - 88

SP - 1574

EP - 1579

JO - Journal of Chemical Education

JF - Journal of Chemical Education

SN - 0021-9584

IS - 11

ER -