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54
TNG HP, PHN TCH PH HNG NGOI (IR)
V PH CNG HNG T PROTON (
1
H-NMR)
CA 3-(8-HIROXIQUINOLIN-5-YL)-1-(3-ETOXIPHENYL)-
PROP-2-EN-1-ON V 1-(4-HIROXIPHENYL)
-3-(8-HIROXIQUINOLIN-5-YL)PROP-2-EN-1-ON

L VN NG
*
, NGUYN TH HONG DUNG
**


TM TT
T 8-hiroxiquinolin, m-metoxiaxetophenon v p-hiroxiaxetophenon, chng ti
tng hp c 3-(8-hiroxiquinolin-5-yl)-1-(3-metoxiphenyl)-prop-2-en-1-on (D
1
) v 1-(4-
hiroxiphenyl)-3-(8-hiroxiquinolin-5-yl)prop-2-en-1-on (D
2
) vi hiu sut tng ng
41,97% v 67,77%, nhit nng chy tng ng 162-164
o
C v 220-222
o
C. Chng ti
phn tch ph hng ngoi IR v ph cng hng t proton
1
H-NMR ca D
1
v D
2
.
ABSTRACT
Synthesizing, analysing spectrum IR and spectrum
1
H-NMR of 3-(8-hydroxyquinolin-5-
yl)-1-(3-methoxyphenyl)-prop-2-en-1-one and 1-(4-hydroxyphenyl)-3-(8-
hydroxyquinolin-5-yl)prop-2-en-1-one
From 8-hydroxyquinoline, m-methoxyacetophenone and p-hydroxyacetophenone, we
synthesize 3-(8-hydroxyquinolin-5-yl)-1-(3-methoxyphenyl)prop-2-en-1-one (D
1
) and 1-(4-
hydroxyphenyl)-3-(8-hydroxyquinolin-5-yl)prop-2-en-1-one (D
2
) with corresponding
efficiency 41.97% and 67.77%, at the melting temperature of 162-164
o
C and 220-222
o
C. We
analyze the IR spectrum and proton magnetic resonance spectrum
1
H-NMR of D
1
and D
2
.

1. M u
[1,2,3]
8-Hiroxiquinolin v dn xut ca
n c kh nng to phc vi cc ion kim
loi, do c s dng rng ri trong
cng ngh ha hc phn tch.
Cc dn xut ca 8-hiroxiquinolin
c bit l dn xut cacbonyl a,b-khng
no l m hnh tt nghin cu s nh
hng qua li gia cc nguyn t trong
phn t.

*
ThS, Khoa Ha hc Trng i hc S phm
TP HCM
**
CN, Trng THPT L Minh Xun, Bnh Chnh,
TP HCM
Dn xut ca 8-hiroxiquinolin c
bit l dn xut cacbonyl a,b-khng no
ca n c tc dng hot tnh chng lao,
chng nm, dit khun nn c s dng
trong y dc lm thuc cha bnh.
2. Thc nghim
2.1. Ha cht v dng c
Ha cht:
- 8-Hiroxiquinolin: 50 gam,
- m-Metoxiaxetophenon: 0,48 gam,
- p-Hiroxiaxetophenon: 0,435 gam,
- Benzen: 500 ml,
- Ancol etylic,
- Dung dch HCl 8% v 36%,
- Dung dch CH
3
COONa bo ha,
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55
- KOH rn: 100 gam,
- Clorofom: 175 ml.
Dng c:
- B Lc di p sut thp,
- B soxhlet,
- Bnh cu 3 c v 1 c,
- My khuy a v t,
- Phu chit,
- ng sinh hn nc,
- Bese,
- Nhit k,
- Phu nh git.
2.2. S tng hp:
(1)
(2)
N
OH
CHCl
3
KOH, C
2
H
5
OH
80
o
C, 12 gi
N
OH
CHO
8-Hiroxiquinolin 5-Fomyl-8-hiroxiquinolin
N
HO
C C
H C
H
O
OCH
3
(Chat D
1
)
N
HO
C C
H C
H
O
OH
(E)-1-(4-hiroxiphenyl)-3-(8-
Hiroxiquinolin-5-yl)prop-2-en-1-on
(Chat D
2
)
(Chat D)
CH
3
C
O
OCH
3
HCl, C
2
H
5
OH, 70
o
C, 6 gi
1)
2) Dung dch CH
3
COONa
ba o ho a
CH
3
C
O
OH
HCl, C
2
H
5
OH, 70
o
C, 6 gi
1)
2) Dung dch CH
3
COONa
ba o ho a
(E)-1-(3-metoxiphenyl)- 3-(8-
hiroxiquinolin-5-yl)-prop-2-en-1-on

2.3. Cch tin hnh tng hp
Giai on (1), tng hp 5-fomyl-8-
hiroxiquinolin (D)
[1,4,5]

Ln lt cho vo bnh cu 3 c
dung tch 1 000 ml gm cc ha cht sau:
5 50 0 g ga am m 8 8- -h hi i r ro ox xi iq qu ui in no ol li in n ( (t ti in nh h t th h k kh h n ng g
m m u u) ), , 2 20 00 0 m ml l e et ta an no ol l, , 1 10 00 0 g ga am m K KO OH H r r n n
t tr ro on ng g 1 12 25 5 m ml l H H
2 2
O O. . L L p p h h t th h n ng g m m y y
k kh hu u y y a a v v n ng g s si in nh h h h n n h h i i l l u u r r i i
u un n c c c ch h t th h y y 8 80 0
o o
C C t tr ro on ng g 1 1 g gi i . . S Sa au u
n nh h t t t t 1 10 00 0 m ml l c cl lo or ro of fo om m v v o o b b n nh h p ph h n n
n ng g t tr ro on ng g 2 2 g gi i 3 30 0 p ph h t t n nh hi i t t 4 45 5
o o
C C. .
T Ti i p p t t c c k kh hu u y y h h n n h h p p p ph h n n n ng g t tr ro on ng g
1 12 2 g gi i n nh hi i t t 8 80 0
o o
C C, , s sa au u c c t t t th hu u h h i i
e et ta an no ol l v v c cl lo or ro of fo om m d d , , t th hu u c c c ch h t t r r n n. .
H H a a t ta an n c ch h t t r r n n t th hu u c c t tr ro on ng g 1 1 5 50 00 0 m ml l
n n c c, , l l c c l l y y d du un ng g d d c ch h. . A Ax xi it t h h a a d du un ng g
d d c ch h l l c c b b n ng g d du un ng g d d c ch h a ax xi it t H HC Cl l. . L L c c
l l y y k k t t t t a a t t c ch h r ra a, , s s y y k kh h r r i i e em m c ch hi i t t
t tr r n n m m y y s so ox xh hl le et t b b n ng g d du un ng g m m i i b be en nz ze en n. .
S Sa au u k kh hi i s so ox xh hl le et t x xo on ng g, , c c t t t th hu u h h i i b be en nz ze en n
t th hu u c c c ch h t t r r n n, , k k t t t ti in nh h l l i i t tr ro on ng g d du un ng g
m m i i r r u u n n c c ( (t th he eo o t t l l t th h t t c ch h 4 4: :1 1) ). .
Giai on (2), tng hp dn xut
xeton aaaa,bbbb-cha no ca 8-hiroxiquinolin
(D
1
, D
2
)
[1,4]

Ln lt c ch ho o v v o o b b n nh h c c u u y y t tr r n n
d du un ng g t t c ch h 1 10 00 0 m ml l g g m m c c c c h h a a c ch h t t s sa au u: :
0,48 gam m-metoxiaxetophenon (hoc
0,435 gam p-hiroxiaxetophenon), , 2 20 0 m ml l
e et ta an no ol l, , 1 13 3 m ml l d du un ng g d d c ch h H HC Cl l 3 36 6% %, , 0 0, ,5 5
g ga am m 5 5- -f fo om my yl l- -8 8- -h hi i r ro ox xi iq qu ui in no ol li in n. . K Kh hu u y y
h h n n h h p p b b n ng g m m y y k kh hu u y y t t 7 70 0
o o
C C
t tr ro on ng g 6 6 g gi i . . C C t t u u i i h h t t e et ta an no ol l r r i i n nh h
t t t t d du un ng g d d c ch h n na at tr ri i a ax xe et ta at t b b o o h h a a c ch ho o
n n d d . . L L c c l l y y c ch h t t r r n n, , r r a a l l i i b b n ng g
e et te e. . K K t t t ti in nh h l l i i b b n ng g d du un ng g m m i i e et ta an no ol l.
3. Kt qu v Tho lun
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56

3.1. Cng thc v tn gi cc cht tng hp c
N
OH
CHO
5-Fomyl-8-hiroxiquinolin
(Cha t D)
N
HO
C C
H C
H
O
OCH
3
(Cha t D
1
)
(E)-3-(8-hiroxiquinolin-5-yl)-1-
(3-metoxiphenyl)prop-2-en-1-on
N
HO
C C
H C
H
O
OH
(E)-1-(4-hiroxiphenyl)-3-
(8-Hiroxiquinolin-5-yl)prop-2-en-1-on
(Cha t D
2
)

3.2. Mt s c im vt l ca cc cht tng hp c
Bng 1


Hp
cht
Dung mi kt tinh Dng b ngoi
Khi lng
Sn phm
(gam)
Hiu
sut
(%)
Nhit
Nng chy
(
o
C)
D V
Ru
:V
Nc
= 4:1
Tinh th hnh kim
mu vng nht
5,1 8,55 172-173
D
1
Etanol
Tinh th
mu vng m
0,37 41,97 162-164
D
2
Etanol Tinh th mu 0,57 67,77 220-222


3.3. c im ph hng ngoi IR (KBr) ca cc cht tng hp c: (xem ph
lc hnh 1, 2, 3)
Bng 2

Hp
cht
n
OH
-

cm
-1

n
CH
no
cm
-1

n
CH

CHO
cm
-1

n
C=O

cm
-1

n
C=C,C=N

(thm)
cm
-1

n
CH

no
n
CH

Trans
cm
-1

n
CH

(khng
phng)
n
CH

(phng)
cm
-1

D 3443 -
2848-
2924
1662
1379-
1612
- -
1280-
1058
628-823
D
1

3462-
3547
2937-
2974
- 1658
1354-
1591
1433
972-
1035
1089-
1327
721-
840
D
2
3298 - - 1645
1375-
1604
-
970-
1033
1155-
1319
464-835

3.4. Ph cng hng t proton
1
H-NMR (500 MHz, DMSO) ca cht D
1
& D
2
(xem
ph lc hnh 4, 5, 6, 7)


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57
Bng 3

chuyn dch ha hc (ppm)
Cht





1
H
C
C C
O
N
HO
H
H
(D
1
)
OCH
3 1
2 3
4
5
6
7
8 9
10
11
12 13

(E)-1-(3-metoxiphenyl)-3-(8-
hiroxiquinolin-5-yl)prop-2-en-1-
on (D
1
).
1
2 3
4
5
6
7
8 9
10
11 12
13
C
C C
O
N
HO
OH
H
H
(D
2
)

(E)-1-(4-hiroxiphenyl)-3-(8-
hiroxiquinolin-5-yl)prop-2-en-1-
on (D
2
).
H
1
8,935 ppm (doublet-doublet) 8,934 ppm (doublet-doublet)
H
2
7,695 ppm (doublet-doublet) 7,686 ppm (doublet-doublet)
H
3
8,766 ppm (doublet) 8,765 ppm (doublet)
H
4
8,353 ppm (doublet) 8,301 ppm (doublet)
H
5
7,209 ppm (doublet) 7,21 ppm (doublet)
H
6
8,465 ppm (doublet) 8,41 ppm (doublet)
H
7
7,918 ppm (doublet) 7,91 ppm (doublet)
H
8
7,246 ppm (doublet-doublet) 8,109 ppm (doublet)
H
9
7,246 ppm (doublet) 6,927 ppm (doublet)
H
10
7,789 ppm (doublet)
H
11
/ 6,927 ppm (doublet)
H
12
7,648 ppm (doublet) 8,109 ppm (doublet)
H
13
3,871 ppm (singlet) 10,371 ppm (singlet)

So snh ph hng ngoi ca 5-fomyl-
8-hiroxiquinolin vi 8-hiroxiquinolin
ta thy trn ph hng ngoi ca 5-fomyl-
8-hiroxiquinolin xut hin mt vch hp
th rt mnh tn s 1662,69 cm
-1
c
trng cho dao ng ho tr ca nhm
C=O, iu chng t phn ng fomyl
ha theo Reimer- Tiemann thnh
cng.
Trn ph
1
H-NMR ca cht D
1

Chng ti nhn thy r nht tn hiu
n c cng tng i bng 3 ng
vi chuyn dch d = 3,871 ppm l ca
cc proton trong nhm metoxi.
vng trng thm, chng ta nhn
thy trn ph xut hin rt nhiu tn
hiu dng vn i. Trong s , c hai
tn hiu c cng tng i bng 1
xut hin chuyn dch d = 8,466
ppm v d = 7,918 ppm c quy kt cho
hai proton H
6

v H
7
. Tn hiu c
chuyn dch d = 8,466 ppm l tn hiu
ca proton H
6
. Tn hiu ny xut hin
trng yu l do s lin hp ca nhm
C=O lm poton H
6
gim chn. ng thi,
do s ghp spin-spin vi proton H
7
nn
tn hiu ny tch i vi hng s tch
3
J =
15,5 Hz. Tn hiu ny c s gim chn t
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58
hn so vi proton H
6
nn xut hin
trng mnh hn. Do c s tng tc
spin-spin vi proton H
6
nn tn hiu ny
cng b tch i vi hng s tch
3
J = 15
Hz.
Da vo hng s tch J mt phn
cng gip chng ti kt lun rng hp
cht tng hp c tn ti dng trans.
Tn hiu d = 8,935 ppm xut hin
trng yu nht vi cng tng
i bng 1, c quy kt cho proton H
1
.
Do s ht in t mnh ca nit nn
proton ny c s gim chn mnh nht.
Nhn thy tn hiu dng vn bn l do
proton H
1
c s ghp spin-spin vi proton
H
2
v H
3
nn tn hiu ny dng doublet-
doublet vi hng s tch tng ng
3
J =
3,5 hz,
4
J = 1 Hz.
Tn hiu xut hin trng yu th
hai vi cng tng i bng 1 l ca
proton H
3
. Do s rt in t ca nit
mnh (-R) nhng khng c hiu ng (I)
nn tn hiu ny chuyn v trng mnh
hn so vi tn hiu proton H
1
, vi
chuyn dch d = 8,769 ppm v ghp spin-
spin vi proton H
2
nn tn hiu ny b
tch i.
Tn hiu xut hin trng mnh
nht trong vng thm d = 7,21 ppm
tng ng vi proton H
5
vi chuyn
dch d = 7,21 ppm. Tn hiu ny xut
hin trng ny l do proton ny v
tr ortho so vi nhm th OH nn b
chn mnh. Do c s tng tc spin-spin
vi H
4
nn tn hiu xut hin dng vn
i vi hng s tch
3
J = 8,5 Hz.
Tn hiu xut hin trng yu hn
H
5
vi chuyn dch d = 7,255 ppm
c quy kt cho proton H
8
. Nhn thy
tn hiu ny c dng doublet-doublet l
do proton H
8
ghp spin-spin vi hai
proton H
9
v H
10
( hoc H
12
) vi hng s
tch tng ng
3
J = 8 Hz,
4
J = 2,5 Hz.
Tn hiu ca proton H
8

yu hn H
5
l do
s rt electron ca nhm C=O v tr
ortho. T mt in tch c phn t
hn proton H
5
.
Tn hiu xut hin vn ba l ca
proton H
9
vi chuyn dch d = 7,505
ppm. L ra tn hiu ny xut hin
doublet-doublet s tng tc ca hai
proton H
8
v H
10
nhng trn ph tn
hiu ny ch xut hin dng vn ba iu
ny c th gii thch do s trng
chuyn dch dn n s chng cc tn
hiu vi nhau. ng thi c s tng tc
vi hai proton bn cnh vi hng s tch
tng ng
3
J = 7,5 Hz,
3
J = 8 Hz.
Tn hiu dng vn bn c quy kt
cho proton H
2
. Tn hiu ny xut hin
chuyn dch d = 7,694 ppm, tng t
vi H
9
proton H
2
cng c s tng tc
vi hai proton H
1
v H
3
bn cnh nn tn
hiu ny cng b tch dng doublet-
doublet vi hng s tch tng ng l
3
J
= 8,5 Hz,
3
J = 9 Hz. So vi H
9
tn hiu H
2

trng yu hn l do b nh hng ca
s rt electron ca d t nit nn proton
H
2
t b chn hn H
9
.
chuyn dch d = 7,648 ppm tng
ng cho proton H
12
. Nhn thy tn hiu
ny tch i rt yu l do s tng tc
vi proton H
10
(hoc H
8
) vi hng s tch
4
J = 2 Hz.
Tn hiu xut hin chuyn dch
chuyn dch d = 7,789 ppm l ca
proton H
10
. Tn hiu xut hin dng vn
i l do tng tc spin-spin vi H
9

c
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59
hng s tch
3
J = 8 Hz. Tn hiu ny xut
hin trng yu hn H
9
l do proton
ny v tr para so vi nhm rt in t
C=O v hiu ng I ca OCH
3
.
Tn hiu cn li dng vn i
tng ng cho H
4
. Tn hiu ny xut hin
chuyn dch d = 8,353 ppm vi dng
vn i do tng tc spin-spin vi proton
H
4
(
3
J = 8 Hz).
Proton ca OH ca vng quinolin
khng th hin trn ph , iu ny c
th gii thch do s to lin kt hiro ni
phn t lm cho tn hiu ca proton dch
chuyn v vng trng thp t 10,0-12,0
ppm v di nh hng ca dung mi
phn cc imetylsunfoxit (DMSO) th n
dch chuyn v vng trng yu hn
ngoi phm vi th hin ca ph .
Phn tch tng t nh vy i
1
H-NMR ca cht D
2

Cht D
1
v D
2
cng l sn phm
ngng t cng mt cht nn l 5-formyl-
8-hiroxiquinolin nn trn ph s c
nhng tn hiu c chuyn dch tng
t nhau (xem bng 3).
S khc bit gia hp cht D
1
v D
2

th hin r nht chuyn dch ca
proton trn vng benzen ca p-
hiroxiphenyl. V y nhm th OH
v tr para lm cho phn t i xng dn
n chuyn dch ca H
11
trng H
9
v
H
8
trng H
12
.
Tn hiu xut hin cng d =
6,927 ppm c quy kt cho proton H
9

v H
11
.
Tn hiu ny xut hin mnh hn so
vi cc tn hiu ca H
8
v H
12
. Do H
9
v
H
11
chu nh hng ca hiu ng ca
hiu ng +R ca i in t t do trn
nguyn t oxi gy ra. Tn hiu ny b tch
i do H
9
(H
11
) tng tc spin-spin vi
H
8
(H
12
) (
3
J = 8,5 Hz).
Tn hiu xut hin chyn dch
d = 8,109 ppm l ca proton H
8
v H
12
.
Hai proton H
8
v H
12
v tr ortho so vi
nhm C=O nn b gim chn mnh do
b dch chuyn v trng yu hn so
vi proton H
9
v H
11
. Do proton H
8
(H
12
)
ghp spin-spin vi proton H
9
(H
11
) nn b
tch i vi hng s tch
3
J = 8,5 Hz.
trng yu c xut hin 1 tn hiu
n v t l ca proton H
13
. Do oxi c
m in ln nn rt in t lm gim
chn mnh t tn hiu ca proton ny
s dch chuyn v pha trng yu.
4. Kt lun
Qu trnh nghin cu, chng ti
hon thnh cc mc tiu t ra cho ti
nghin cu t kt qu sau :
Tng hp thnh cng 5fomyl8
hidroxiquinolin t 8hidroxiquinolin vi
tc nhn fomyl ha CHCl
3
/KOH theo
phn ng Reimer Tiemann, hiu sut
t 8,55%, ph hp vi ti liu [1] v [2]
cng b.
tng hp 3-(8-hiroxiquinolin-
5-yl)-1-(3-metoxiphenyl)-prop-2-en-1-on
v 1-(4-hiroxiphenyl)-3-(8-
hiroxiquinolin-5-yl)prop-2-en-1-on bng
phn ng ngng t anol croton ha
vi xc tc axit v c t hiu sut tng
ng l 41,97% v 67,77%.
xc nh cc thng s vt l ca
cc cht tng hp c, xc nh nhit
nng chy v dung mi ha tan ca
chng.
o ph hng ngoi IR v ph
cng hng t proton
1
H-NMR ca cc
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60
cht D
1
v D
2
, tin hnh phn tch ph,
xc nh, quy kt cc vn c trng cho
cc nhm chc c bn v chng minh
c cc hp cht xeton a,b - cha no D
1

v D
2
u c cu hnh trans.
Chng ti cha tm thy ti liu no
trong s cc ti liu tra cu c cp
n ph IR v ph
1
H-NMR ca cc cht
D
1
v D
2
.

TI LIU THAM KHO
1. L Vn ng, Nguyn Th Thng (2010), Tng hp, phn tch, ph hng ngoi
(IR) v ph cng hng t proton (
1
H-NMR) ca 1-(4-clorophenyl)-3-(8-
hiroxiquinolin-5-yl)prop-2-en-1-on v 3-(8-hiroxiquinolin-5-yl)-1-(4-
nitrophenyl)prop-2-en-1-on, Tp ch Khoa hc Trng i hc S phm TP HCM,
21(55), tr. 109-115.
2. Nguyn Xun Giang (1982), Tng hp mt s dn xut xeton b a , khng no ca hp
cht d vng, Lun n Tin s.
3. Trn Quc Sn (1988), Tng hp, nghin cu cu trc v tnh cht b-(6-
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5. Robert Thornton Morrison and Robert Neilson Boyd (Professors of Chemistry New
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KHO ST TINH DU G LONG NO,
(Tip theo trang 45)

17. Brett J. Stubbs, Alison Specht, Don Brushett (2004), The essential oil of
Cinnamomum camphora (L.) Nees and Eberm. Variation in oil composition
throughout the tree in two chemotypes from Eastern Australia, Journal of Essential
Oil Research, 16(3), pp. 200-205; Brett J. Stubbs, Don Brushett (2001), Leaf oil of
Cinnamomum camphora (L.) Nees and Eberm. from Eastern Australia, Journal of
Essential Oil Research, 13(1), pp. 51-54.
18. (a) Naito Tsutomu (1943), The constituents of the volatile oil from the leaf of
Cinnamomum camphora var. glaucescens, Nippon Kagaku Kaishi, 64, pp. 1125-
1129; (b) Fujita Yasuji, Fujita Shinichi, Nishida Setsuo (1974), Biogenesis of the
essential oils in camphor trees. XXXI. Components of young and old shoot oils of
Cinnamomum camphora var linaloolifera, Osaka Kogyo Gijutsu Shikensho Kiho,
25(4), pp. 244-246; (c) Renzo Hattori (1981), Camphor tree and ho wood [essential
oils], Koryo, 134, pp. 83-90; (d) Naonori Hirota (1954), The oil of every part of the
East camphor tree, Perfumery and Essential Oil Record, 45, pp. 5-9.

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