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Agricultural and Biological Chemistry

ISSN: 0002-1369 (Print) (Online) Journal homepage: http://www.tandfonline.com/loi/tbbb19

3S-(+)-3,7-Dimethyl-1,5,7-octatriene-3-ol in the
Essential Oil of Black Tea

Yoichi Nakatani, Sumiko Sato & Tei Yamanishi

To cite this article: Yoichi Nakatani, Sumiko Sato & Tei Yamanishi (1969) 3S-(+)-3,7-
Dimethyl-1,5,7-octatriene-3-ol in the Essential Oil of Black Tea, Agricultural and Biological
Chemistry, 33:6, 967-968, DOI: 10.1080/00021369.1969.10859406

To link to this article: https://doi.org/10.1080/00021369.1969.10859406

Published online: 09 Sep 2014.

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Short Communication

[Agr. Bioi. Chern., Vol. 33, No. 6, p. 967-968, 1969]

3S-( + )-3,7-Dimethyl-1,5,7-octatriene-3-ol m the Essential


Oil of Black Tea"

Sir: relative retention time to that of linalool was


Extensive studies on the neutral fraction of 1.27 on the column of Carbowax 20M, and
the essential oil 21 from black tea have been the IR, NMR and mass spectra were com-
carried out by Yamanishi et al. with fractional pletely identical with those of authentic 3, 7-
distillation, silica-gel column chromatography dimethyl-1,5,7-octatriene-3-ol, which was re-
and gas chromatography* cently isolated from the essential oil of Ho-leaf
In this paper we wish to report the isolation by Muraki. 4 ' However, the former has the
of a component with a very sweet and flowery specific rotation + ll.9°, while the latter has
aroma, which has never been reported as a [a]~-15.2°
constituent of black tea up to date. 31 In order to determine the absolute configu-
The compound seems to be one of the im- rations* at C-3 of these compounds, (- )-linalyl
portant constituents of black tea flavor. The acetate (l), [a]t0 -10.8°, was transformed into

100
90
,.,--, ... --- -
.s" 70 :'
"'"' 60
''
~ 50
E
40
:!
~,J
0~ 30
20
10
4000 3600 3200 2800 2400 2000 1900 1800 1700 1600 1500 1400 1300 1200 1100 1000 900 800 700 600
1
\\'a\'e numher I em )

FIG. 1. Infrared Spectra of Natural and Synthetic 3R-(- )-3, 7-dimethyl-1 ,5, 7-octatriene-3-ol (neat film).
Full line: Natural one
Broken line: Synthetic one

* Experimental parameters of GLC were as fol- 3) T. Yamanishi, Eiyo to Shokuryo, 21, 227 (1968).
lows; 4) S. Muraki, The 11th Symposium on the Chemis-
Column: 3 mm X 187 em stainless steel, try of Terpenes, Essential Oils and Aromatics, Matsu-
Carbowax 20M 2396 on Chromosorb W yama, Japan, Oct., 1967, p. 30.
60/80, 5) G. Ohloff und E. Klein, Tetrahedron, 18, 37 (1962).
Carrier gas: Helium, 20 mlfmin, 6) R. S. Mulliken, ]. Chern. Phys., 7, 121 (1939).
Column Temp.: 15ooc. * After this article was accepted, T. Yoshida et al.
1) T. Yamanis~i, A. Kobayashi, H. Nakamura, reported the determination of the configuration of
A. Uchika, S. Mon, K. Osawa and S. Sasakura, Agr. (- )-trans-Hotrienoi: T. Yoshida, S. Muraki, H. Kawa-
Biol. Chern., 32, 379 (1968). mura and A. Komatsu, Agr. Biol. Chern., 33, 343
2) T. Yamanishi, T. Kiribu~hi, M. Sakai, N. (1969).
Fujita, Y. Ikeda and K. Sasa, tbtd., 27, 193 (1963).
968 Y. NAKATANI, S. SATO and T. YAMANISHI

OCOCH, " OCOCH, = OCOCH, ~ OCOCH,

Nss+n+n+n

B~ ~BrBr~
I
(R -configuration) (R -configuration l

6'"/
~Oil
nOCOCH,

~ --:K:-:'O'""H----'""

II
(R- configuration) (R- configuration) (R- configuration)

FIG. 2. Synthesis of 3, 7-Dimethyl-1 ,5, 7-octatriene-3-ol.

HO-Leaf Oil tion (!-form; .{~'.?xH 230 mp, log s4.4 and d-form:
A:;;~: 230 mp, log s4.3) of these compounds in-
dicate that their conjugated double bonds exist
in the S-trans conformation.
It is very interesting that both linalool and
(3R)-(-) (3R)-(-) 3, 7-dimethyl-1 ,5, 7-octatriene-3-ol in black tea
have 3S-configuration, while those in Ho-leaf
Black Tea
have 3R-configuration. This fact as well as the

~·------• ~OH easy transformation described above indicates


that these 3,7-dimethyl-1,5,7-octatriene-3-ols
were respectively derived from the correspond-
ing linalools in the manufacturing process or
(3S)-( +) (35)-(+)
in plants themselves (Fig. 3).
FIG. 3. Probable Biosynthetic Pathway of 3,7- The authors wish to thank Mr. Shigeru
Dimethyl-l ,5, 7-octatriene-3-ol. Muraki (Takasago Perfumery Co. Ltd.), Pro-
fessor Akio Kobayashi (Tohoku University)
(- )-3,7-dimethyl-1,5,7-octatriene-3-ol (II), [a)~ 0 and Dr. Y oshiaki Tanahashi (U niversite de
-3.0°, via a mixture of bromides (Figs. 1, 2). Strasbourg) for their valuable discussion.
Since I was shown to be 3R-configuration on Yoichi NAKATANI
alkaline hydrolysis to 1-linalool (III), [a]~ - 0
Sumiko SATO
10. 7o, it is concluded that II has 3R-configu- Tei YAMANISHI
ration and the corresponding (+)-form has Laboratory of Food Chemistry
3S-configuration. This is also the first synthesis Ochanomizu University
of this structure to our knowledge. Bunkyo-ku, Tokyo
Furthermore, the intensities of UV absorp- Received March 22, 1969