Anal Bioanal Chem (2004) 380: 734–735

DOI 10.1007/s00216-004-2820-x

A NA L YT I C A L C H A L LE N G E

Silvia Paasch Æ Reiner Salzer

Solution to Spectroscopy Challenge 7

Published online: 28 October 2004

Ó Springer-Verlag 2004
many other biological processes. Because the human
The winner of the seventh spectroscopy challenge (pub- body cannot produce vitamin C himself, ascorbic acid
lished in issue 379/5) is: Dr. Juris Meija, University of Cin- must be ingested every day. Good sources of Vitamin C
cinnati, USA. are citrus fruits, berries, green leafy vegetables, paprika,
The award entitles the winner to select a Springer- tomatoes, melons, kiwi fruits, etc. In addition, a variety
Verlag book from our catalogue up to a value of € 75,-. of Vitamin C pharmaceutical products are available.
Our Congratulations! 13
C NMR spectra
In the 1H-decoupled 13C NMR spectrum there are six
Solution signals (Table 1), the signal at 39.5 ppm is from the
solvent DMSO, and is disregarded.
Ascorbic acid, L-ascorbic acid, vitamin C The DEPT spectrum contains three signals only, two
positive (68.4 and 74.6 ppm) and one negative at
61.9 ppm.
1
H NMR spectrum
In the 1H NMR spectrum seven signals appear (Ta-
History The name ascorbic acid comes from word ble 2), the peaks at 4.73 and 3.45/3.43 ppm are shown
‘‘anti-scurvy’’ acid. separately. The splittings of the signals are not very
informative because most are high-order.
1
Ascorbic acid or vitamin C was discovered after sci- H/1H COSY spectrum
entists had searched for centuries for a drug to cure the The most important information is the interaction of
disease known as scurvy. This disease was caused by a the proton of the signal at 3.74 ppm with the protons of
serious deficiency of vitamin C and often plagues sailors, the signals at 3.45/3.43, 4.73, and 4.89 ppm.
explorers, and armies. The Scottish naval surgeon James Possible structural element:
Lind treated scurvy. As a consequence in 1795 daily
doses of lime juice were prescribed for all the sailors in OH
the British navy and scurvy quickly vanished. CH
In 1928, the Hungarian scientist Albert Szent-Gy- -O-CH
örgyi isolated ascorbic acid for the first time. Five years CH2-O-
later the chemical structure of vitamin C was determined Mass spectrum
by the English chemist Walter Norman Haworth. The molecular ion appears at m/z=176.
IR spectrum
Importance Ascorbic acid is a powerful antioxidant The IR spectrum contains typical bands for func-
and helps protect the body against pollutants. It is re- tional groups, e.g. C=O (1754 cm 1) and OH (several
quired in the synthesis of collagen in connective tissue, bands between 3600 and 2700 cm 1).
neurotransmitters, steroid hormones, carnitine, and
3526, 3411, 3316, 3217, 3029, Broadened mOH bands
S. Paasch Æ R. Salzer (&) 2730 cm 1 mCH CH3, CH2 or CH group
Department of Analytical Chemistry, 2916 cm 1 mC=O ester
University of Dresden, 01062 Dresden, Germany 1754 cm 1 mC=C or mC=O
E-mail: reiner.salzer@chemie.tu-dresden.de 1673 cm 1 mC–O–C ester
Tel.: +49-351-46332631 1274+1129 cm 1
Fax: +49-351-46337188
 735
13
Table 1 Relevant C NMR signals

d [ppm] 170.7 152.9 117.9 74.6 68.4 61.9

Structural Quaternary atom Quaternary C atom Quaternary C atom CH group CH group CH2 group
information COOH or COOR C with double bond C with double -CH–O- -CH–O- -CH2–O-
bond, or aromatic

Table 2 Relevant 1H NMR signals

d [ppm] 11.03 8.31 4.89 4.73 3.74 3.45/3.43

Multiplicity Singlet Singlet Broad signal, Doublet High order Two signals
no splitting visible high order
Intensity 1 1 2 1 1 2
Structural information -COOH-OH -OH -OH-CH–O- -OH-CH–O- -OH-CH–O- -CH2–O-
(possibilities)

Interpretation The 1H NMR signal at 4.73 ppm is split into a

After interpretation of the IR spectrum the presence doublet. This means that one proton is located in
of two different C=O groups is possible. However this is immediate vicinity of this proton. Also, in accordance
not in agreement with the information from the 13C with the results of the COSY spectrum both structural
NMR spectrum, in which only one signal appears in the elements can combined to give:
specific region (170 ppm). Therefore the compound only
has one COOR group according to 13C NMR and IR.
Hence, the OH peak at 11.03 ppm in the 1H NMR
spectrum is not derived from an acid (Table 3).

Table 3 Interpretation