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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

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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:

Extensive studies on the neutral fraction of the essential oil 21 from black tea have been carried out by Yamanishi et al. with fractional distillation, silica-gel column chromatography and gas chromatography* In this paper we wish to report the isolation of a component with a very sweet and flowery aroma, which has never been reported as a

constituent of black tea

The compound seems to be one of the im- portant constituents of black tea flavor. The

up to date. 31

relative retention time to that of linalool was 1.27 on the column of Carbowax 20M, and the IR, NMR and mass spectra were com- pletely identical with those of authentic 3, 7- dimethyl-1,5,7-octatriene-3-ol, which was re-

cently isolated from the essential oil of Ho-leaf

by Muraki. 4 ' However, specific rotation + ll.9°,

the former has the while the latter has

[a]~-15.2°

In order to determine the absolute configu- rations* at C-3 of these compounds, (- )-linalyl acetate (l), [a]t 0 -10.8°, was transformed into

FIG.

 

100

90

"

.s

70

"' "'

60

'

 

'

 

50

 

:!

 

E

40

0~ 30

20

10

,.,--,

:'

---

-

4000

3600

3200

2800

2400

2000

1900

1800

1700

\\'a\'e

1600

1500

numher

1400

I em

1 )

1300

1200

1100

1000

900

800

700

600

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

*

lows;

Experimental

parameters of GLC

were

as

fol-

Column:

3 mm X 187 em stainless steel, Carbowax 20M 2396 on Chromosorb W

60/80,

Carrier gas:

Column Temp.:

Helium, 20 mlfmin,

15ooc.

Nakamura,

A. Uchika, S. Mon, K. Osawa and S. Sasakura, Agr.

1)

T. Yamanis~i, A.

Kobayashi,

H.

Biol.

Chern., 32, 379 (1968).

 

2)

T.

Yamanishi,

T. Kiribu~hi, M. Sakai,

N.

Fujita, Y. Ikeda and K. Sasa, tbtd., 27, 193 (1963).

3) T. Yamanishi, Eiyo to Shokuryo, 21, 227 (1968).

S. Muraki, The 11th Symposium on the Chemis-

try of Terpenes, Essential Oils and Aromatics, Matsu-

yama, Japan, Oct., 1967, p. 30. 5) G. Ohloff und E. Klein, Tetrahedron, 18, 37 (1962).

4)

6)

*

R. S. Mulliken, ].

Chern.

Phys., 7,

121 (1939).

After this article was accepted, T. Yoshida et al. reported the determination of the configuration of (- )-trans-Hotrienoi: T. Yoshida, S. Muraki, H. Kawa- mura and A. Komatsu, Agr. Biol. Chern., 33, 343

(1969).

968

Y. NAKATANI, S. SATO and T. YAMANISHI

OCOCH,

"

OCOCH,

= OCOCH,

OCOCH,

~

Nss+n+n+n

I

(R -configuration)

B~

~BrBr~

(R -configuration l

6'"/

nOCOCH,

~

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

~Oil

(R- configuration)

(R- configuration)

II

(R- configuration)

FIG. 2.

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

HO-Leaf Oil

(3R)-(-)

Black Tea

(3R)-(-)

~·------•~OH

(3S)-( +)

(35)-(+)

FIG. 3.

Biosynthetic

Dimethyl-l ,5, 7-octatriene-3-ol.

Probable

Pathway

of

3,7-

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 3,7-dimethyl-1 ,5, 7-octatriene-3-ol in black tea have 3S-configuration, while those in Ho-leaf have 3R-configuration. This fact as well as the 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 in plants themselves (Fig. 3). The authors wish to thank Mr. Shigeru Muraki (Takasago Perfumery Co. Ltd.), Pro- fessor Akio Kobayashi (Tohoku University)

(- )-3,7-dimethyl-1,5,7-octatriene-3-ol (II), -3.0°, via a mixture of bromides (Figs. 1, 2). Since I was shown to be 3R-configuration on

alkaline hydrolysis to 1-linalool (III), [a]~ 0 -

that II has 3R-configu-

ration and the corresponding (+)-form has 3S-configuration. This is also the first synthesis of this structure to our knowledge. Furthermore, the intensities of UV absorp-

0 and Dr. Yoshiaki Tanahashi (Universite de Strasbourg) for their valuable discussion.

Yoichi NAKATANI

[a)~

Sumiko SATO

Tei YAMANISHI

10. 7o, it is concluded

Laboratory of Food Chemistry Ochanomizu University Bunkyo-ku, Tokyo

Received March 22, 1969