HP CHT THIN NHIN

Acid nucleic
Terpenoid

Steroid
Alcaloid

LA CHN DUNG MI CHIT TCH HP CHT

Eter dau hoa Hexan Benzen

Alcan Alcen, alcin >C=C< ; -CC-

Dung moi co tnh phan cc tang dan

Toluen Diclorometan Cloroform Etyl acetat Etanol Metanol Butanol Nc

Hp chat thm
Eter O

Aldehyd, Ceton -CHO, -COEster, amid -COOR, -CONH2 Hydroxy, amin -OH, -NH2 Acid carboxylic -COOH

Nhomc hc co tnh phan cc tang dan

CC K THUT CHIT TCH HP CHT RA KHI CY

CHIT LNG-LNG

CHIT RN-LNG

- NGM KIT - NGM DM - TRCH VI MY Soxhlet

CHIT LNG-LNG

Nguyen tac: da vao s phan bo cua mot chat tan vao hai pha
long ma hai pha long nay khong tan vao nhau.
Pha hu c (cha hp chat tan tot trong pha hu c) Pha nc (cha cao alcol ban au)

CHIT LNG-LNG

Nhc iem: dung moi trong bnh long tao nhu tng, gay kho khan cho viec tach thanh 2 lp. Khac phuc: - S dung ua thuy tinh, khuay nhe cho mat thoang cua dung dch nham pha v cac bot kh e dung dch nhanh chong phan thanh 2 lp.

- S dung muoi NaCl, acetonitril, toluen

CHIT RN-LNG

1. K THUT CHIT NGM KIT

2. K THUT CHIT NGM DM

3. K THUT CHIT BNG MY SOXHLET

1. K THUT CHIT NGM KIT

Dung mi tinh khit

Giy lc

x x x xx xx x x x x x x x xx x x

Vin bi thy tinh Bt cy Bng thy tinh

Dung dch chit

2. K THUT CHIT NGM DM

Giy lc

Phu thy tinh Dung mi xp xp

x xx x x x x x x x x x x x x x x x x xx x x x x x x x x

Bt cy
Bnh thy tinh

Dung dch chit qua lc

3. K THUT CHIT BNG MY SOXHLET

ng ngng hi C

Nt mi (3)
Ti vi cha bt cy Nt mi (2)

ng B Vin bi thy tinh

ng E

Nt mi (1) Dung mi

A
Bp un

May co quay chan khong

MT S TH THUT KHI C LP HP CHT HU C

1. LAM KHO MAU

- Cac hp chat trong cao se on nh ben neu chung hien dien trang thai kho hn la trang thai long. - e tnh ung thu suat. - e tiep tuc tinh che bang sac ky cot. - Thuan li cho viec giai oan cau truc.

1.1 LAM KHO MAU NH BNH HUT AM

Nap bnh bang nut mai

Gan vao may bm hut

Mau can lam kho

Becher co nap la t giay loc b uc lo

Chat lam kho

V sanh co uc lo e ngan bnh hut am thanh 2 ngan

1.2 LAM KHO MAU BANG KY THUAT ONG KHO CHAN KHONG

(Thng ap dung cho mau la dch chiet bang nc)

- Dch chiet c ong ac thanh a cuc nh hon hp lanh alcol-CO2 ran.

- Lap bnh cau vao may ong kho chan khong, he thong may ha nhiet o xuong -800C , chan khong sau, ke o nhiet o c tang len t t.
- Nc se boc hi het ra khoi bnh. Sau khoang 24h trong bnh ch con mau dang kho ti xop.

2. S KET TINH LAI

- Hoa tan tot chat can tinh che khi un nong va chat nay se khong tan hoac t tan khi dung moi lanh. -Tap chat phai tan nhieu trong dung moi lanh, khong tan trong dung moi nong. - Co nhiet o soi thap. - Khong tng tac hoa hoc vi chat can tinh che.

SC K LP MNG
Np y bng king T giy lc Bn mng im chm mu * Bnh sc k * Pha tnh * Pha ng * Mu cht cn phn tch Mc xut pht Mc dung mi trong bnh

Mc tin tuyn dung mi

S tng tc gia hp cht cn phn tch vi pha tnh v pha ng

Lc ht ca pha tnh i vi cht tan - Nu cht tan l loi hp cht c tnh phn cc mnh th s b silica gel/alumin hp thu mnh, gi cht.( )

- Nu cht tan l loi hp cht c tnh phn cc trung bnh, lc nu gi ca silica gel/alumin ty thuc vo phn cc ca dung mi gii ly.( )
- Nu cht tan c tnh km phn cc th b silica gel/alumin hp thu km.( )

S tng tc gia hp cht cn phn tch vi pha tnh v pha ng

Lc li ko ca dung mi i vi cht tan

- Nh ha tan.
- Hin tng thay th ch.

CC CNG DNG CA SC K LP MNG

cng b c im ca hp cht va chit tch c lp

b a

on ng di chuyn ca hp cht a Rf = = b on ng di chuyn ca dung mi

 kim tra xem hai hp cht c ging nhau khng?

E : C 3:7

C : AE 4:6

C : M 8:2

Bit s b s lng v thnh phn phn trm ca cc hp cht c trong mu ban u

Kim tra tinh khit ca mt hp cht (thc hin ging nh phn xem hai cht c ging nhau khng)

Theo di din tin ca mt phn ng tng hp hu c

A +B C

B
A C B Bt u phn ng A C B
Sau 10

A C B
Sau 20

A C B
Sau 30

A C B
Sau 40

- chun b cho vic sc k ct

- kim tra xem hp cht c km bn hay khng - c lp hp cht

ACID NUCLEIC
Acid nucleic l mt polyester ca acid phosphoric + ng pentose + base hu c.
Base ng Base ng

O O P O O

O O P O O

Nucleosid

Nucleotid

Phn ng : D(-) ribose v D(-)-2-deoxyribose. Phn base : purin v pyrimidin.

PHN NG CA ACID NUCLEIC

1

CHO OH OH OH

2 3
4 5

HOH2C
4

O H
3

OH H
2 1

Acid Ribo Nucleic (ARN)

H H

CH2OH

OH

H OH

D(-) Ribose
1

-D(-) - Ribofuranose

CHO H OH OH
4

2 3
4 5

HOH2C H
3

O H
2

OH
1

Acid Deoxyribo Nucleic (ADN)

H H

OH

CH2OH

D (-)-2-Deoxyribose

-D(-) 2-Deoxyribofuranose

PHN BASE CA ACID NUCLEIC 1. Cc base purin

6 1

N N
3

N
5 4

Purin
N H
O H
1 6

NH2
6 1

NH2 N
5 1 6

H N
5

O H
1 6

H N
5 4

N N
3

N N
3

N
2

N
2

N
5 4

N H

H2N

N
3

H2N

N
3

N H

Adenin

Guanin

NH2 CH3 N
2 1 6 5 4

H N N

CH3NH N
2 1 6 5

O
H N
4

H N
5 4

O H
1 6

H N
5 4

O CH3
1 6

H N
5 4

H
1

N
2

N
2

N
2

N
3

N
3

CH3HN

N
3

(CH3)2N

N
3

H2N

N
3

1-Metiladenin

6-metilaminoadenin

2-Metilaminoguanin

2-Dimetilaminoguanin

1-Metilguanin

2. Cc base pyrimidin

N N

O H O
1 6 5 4 3

NH2 N O N H
Cytosin
H O N

O CH3 N H

N
2

N H

Uracil

Thymin

Tm li, c th chia acid nucleic thnh 2 loi ln: + Acid ribonuleic (ARN): khi thy phn cho D-ribose, acid photphoric, adenin, guanin, cytosin, uracil.

+ Acid deoxyribonucleic (AND): khi thy phn cho D-2deoxyribose, acid photphoric, adenin, guanin, cytosin, thymin.

CU TO CA CC NUCLEOSID
Nucleosid l t hp gia ng ribose hoc deoxyribose vi cc base purin hoc pyrimidin. Adenosin (Ribose + Adenin)

Guanosin (Ribose + Guanin)

Thymidin (Deoxyribose + Thymin) Cytidin (Ribose + Cytosin)

Uridin (Ribose + Uracil)

Cu to :
1

NH2
6

N N
3

N7 N9

6 1

7 5

N N
3

N N
9

H 2N HOH2C

HOH2C H H OH

O H H OH

O H H H OH

H OH

Adenosin (Ribose + Adenin)

Guanosin (Ribose + Guanin)

Lin kt glycosid

O H O HOH2C H H OH H N
3

NH2
CH3

O H N

N
3

O HOH2C O H H

N
HOH2C H H OH

O O H

O H H

H OH

H OH

H OH

Thymidin (Deoxyribose + Thymin)

Cytidin (Ribose + Cytosin)

Uridin (Ribose + Uracil)

CU TO CA NUCLEOTID
Nucleotid l nucleosid photphat.
NH2
6 1

O H

N N

N7 N9
HOH2C O O H
3

N N

HOH2C H
3

O H H OH

H H OH

H O O P OH OH

H O O P OH OH

Adenosin phosphat

Uridin phosphat

CU TO CA ACID NUCLEIC

7 8 9 4 3 2

6 1 1 3

TERPENOID
Terpen l nhng hydrocarbon c cng thc chung l bi s ca phn t isopren (C5H8)n
n CH2 C CH CH2 CH3
Isopren

CH2 C CH CH2 CH3

ui

ui

Monoterpen

(C5H8)n n=1 C5H8 Hemiterpen (isopren)

n=2
n=3 n=4

C10H16
C15H24 C20H32

Monoterpen
Sesquiterpen Diterpen

n=5
n=6 n=n

C25H40
C30H48 (C5H8)n

Sesterterpen
Triterpen Polyterpen (cao su thin nhin)

MONOTERPEN C10H16

Monoterpen khng vng (c 3 lin kt i) Monoterpen 1 vng (c 2 lin kt i) Monoterpen 2 vng ( c 1 lin kt i)

 Monoterpen khng vng (c 3 lin kt i)

3 4 5 6 2 1

- Tinh du cy Myrcia acris. - Cht lng, ts = 166-168oC

7
8

- Ozon gii

(CH3)2C=O,

Myrcen

HOC(CH2)2COCHO, HCHO

(7-Metil-3-metilenocta-1,6-dien)

3 4 5 6 2 1

- Tinh du l hng qu (Ocimum basilicum). - Cht lng, ts = 81oC/30mmHg

- Ozon gii CH3COCHO, HCHO Ocimen HOCCH2CH2COCH3

7
8

(3,7-Dimetilocta-1,3,7-trien)

CC DN XUT CA MONOTERPEN KHNG VNG

Dn xut alcol
3 4 5 6 2

CH2OH
4 5

3 2

CH2OH
1

trans

cis

Geraniol
OH
2 1 6

Nerol

3 4 5

3 4 5 6 2

CH2OH
1

Linalol

Citronellol

(5 tan)

1 kg tinh dau

30-40% Geraniol
3 4 5 6 2

35-55% Citronellol
3 4 5 6 2

5-10% Nerol
3 4 5 6 2

Cac thanh phan khac

CH2OH

CH2OH
1

CH2OH
1

 Dn xut aldehyd
1 3 4 5 6 2

CHO
4 5

3 2
4 5

3 2

CHO
6 1 7

CHO
6 1 7

Geranial, Citral a

Neral, Citral b

Citronellal

iu ch Citral b trong cng nghip:

BrH2C O C CH3 CH3 C2H2 NaNH2 HC C C H3C CH3 OH H2/Pd H2C=HC C H3C CH3 OH
C2H5OOC

PBr3 H3C

C CH3 HBr

C2H5OOC

OH O H O, HO2 O
ClCH2COOC2H5
-H 2O

1.DIBAH + 2. H3O

Zn

COOC2H5

COOC2H5

CHO

Citral b

CH3 CHO
(CH3)2CO H2O

CH3 H H
+

CH3 C H H O

Citral a
CH3 C O

CH3 C H O

-Ionon

-Ionon

Vitamin A

BrCH2CN Zn

CN OH

COOH H2O
1.

ROH (H+) 2. LiAlH4 3. MnO2 CHO

COOR (C6H5)3P

CH3 CH C CH COOR

LiAlH4

CH2OH

Vitamin A : - Chat ket tinh mau vang, t0nc = 640C.

Vitamin A

- Giup sang mat.

- Lan au tien c tm thay trong dau gan ca (1931). - Co nhieu trong gan ca va long o trng.

 Monoterpen 1 vng (c 2 lin kt i)

7 6 1 2 3

Khung p-mentan

8
10

Limonen

-Terpinen
1,8

-Terpinen

-Terpinen

Terpinolen

-Phelandren -Phelandren

1,8-Mentadien (

-Mentadien)

CC DN XUT CA MONOTERPEN MT VNG

Dn xut alcol
OH

OH

O
OH

Menthol

cis-Terpin-1,8

Cineol-1,8

3-Hydroxi-p-mentan

1,8-Dihydroxi-p-mentan

1,8-epoxi-p-mentan

T -Pinen (thnh phn chnh trong tinh du thng) iu ch -Terpineol, cis-Terpin-1,8, Cineol-1,8.
OH

-Terpineol

OH

CH3

CH(CH3)2 OH
CH3 OH

CH(CH3)2

CH3 OH

CH(CH3)2

CH(CH3)2 OH CH3

OH H+ H2O H+ OH H2 O H2O

O
OH

-Pinen

-Terpinol
OH OH

cis-Terpin-1,8

Cineol-1,8

cis-Terpin-1,8

OH

trans-Terpin-1,8
OH H+

H2O H O

H2O

OH

CH3

Cineol-1,8

 Monoterpen 2 vng (c 1 lin kt i)

2 1 6 7 5 4 3

Pinan

Thuyan

Caran

Camphan (Bornan)
7

Fenchan

6
6 4 5 1 2

1 5

2,6,6-trimetilbicyclo[3.1.1]heptan

1,7,7-trimetilbicyclo[2.2.1]heptan

 Nhm pinan
10
2 1
10 2

8
6

1 6

8 9

3 4

7 5

7 5

-Pinen

-Pinen

Nhm Camphan
10 1 6 8 7 5 4 3 9 2

9 10

O
6 4 5

1 2 3

Camphor

SESQUITERPEN C15H24

Sesquiterpen khng vng (c 4 lin kt i)

Sesquiterpen 1 vng (c 3 lin kt i) Sesquiterpen 2 vng (c 2 lin kt i)

Sesquiterpen 3 vng (c 1 lin kt i)

-Facnesen (c trong tinh du s)

-Salinen (c trong tinh du cn ty)

OH

OH

Punctaporonin A
HOH2C

DITERPEN C20H32
Diterpen khng vng & Diterpen vng
Diterpen khng vng
1 16 11 7 3 2

CH2OH

Phytol (2E-7R,11R)-3,7,11,15-Tetrametilhexadeca-2-enol

O CH3

gc Phytyl

Vitamin K1 (2-metil-3-phytyl-1,4-naphtoquinon)

 Diterpen vng
1 11 2 10 9

A
3 12 4

B
13 8

C
5 6

1-metil-7-isopropilphenanthren
CH3 COOH

CH3

COOH

CH3

CH3

Acid Abietic

Acid Sapietic

POLYTERPEN (C5H8)n
@ Cao su thin nhin
CH3 CH2 C CH CH2 n

Polyisopren

CH2 C C CH3

CH2 CH2 H

CH2 CH2 CH2 C C C C H CH3 H CH3

Cao su thin nhin (dng cis)

CH3 C CH2 C

CH2 H

CH2 C CH3

H C

CH3

CH2

CH2

C C H CH2

Nha Kt (gutta-percha) - dng trans

 Lu ha cao su: chuyn cao su t trng thi mch thng

sang trng thi khng gian 3 chiu. * Lu hunh

* Selen
* Peroxit Mc ch : lm cho cao su bn hn, dai hn v a cao su tr thnh sn phm c ng dng rng ri trong cuc sng. Tnh n hi cao su: + Nh qu trnh lu ha

+ Do cu hnh cis

@ Cao su tng hp
Cao su Buna (1,3-butadien), cao su Buna-N (butadien-1,3 + vinylcianid), cao su Buna-S (butadien1,3 + styren). Cao su Neopren (2-clorobutadien-1,3).

@ Cao su silicon
Si(CH3)2 O Si(CH3)2 O

STEROID

Khung gonan (1,2-cyclopentanoperhydrophenanthren)

Sterol Acid mt Ni tit gii tnh Ni tit thng thn (Cortinoid) Glycosid tim Sapogenin Steroid alcaloid

@ Cch nh s
21 22 20 18 12 17 23 26

12 11 1 10 2 9 13

17

C
14 8 7

D
15

16
1 2 3

11 19 9 14 10 8 7 5 4 6 15 13 16

24

25 27

A
3 5 4

B
6

HO

Cholesterol

@ Ha lp th ca khung gonan - Khung gonan c 6 C* . - Vng B&C, C&D : trans; A&B : trans hay cis.

A&B: trans
A&B: cis

dy (allo)
dy (normal)

13

C A B

A&B: trans dy (allo)

13

C B A

A&B: cis dy (normal)

- Cc nhm th hng ln mt phng trung bnh c cu hnh , ngc li l , nhng ni cha xc nh c cu hnh . - Nhm th ti C13 lun hng ln (cu hnh ).

STEROL
- Sterol c trong m ng vt, du thc vt. Cht kt tinh. - Cholesterol, cholestanol, coprostanol : sterol ng vt.

- Ergosterol, stigmasterol : sterol thc vt.

- Sterol vi sinh vt : tch t nm, mc.

HO

HO

Cholesterol

Stigmasterol

1. CHOLESTEROL (C27H46O)
-Tinh th, tnc= 149oC, []D= -39 - Cholesterol c vai tr quan trng trong s hnh thnh cu trc t bo v kch thch t (hormon).
HO

Cholesterol

- Cholesterol lin kt vi lipoprotein LDL v HDL lu hnh trong mu. LDL chuyn cholesterol ti cc t bo, HDL chuyn cholesterol v gan bi tit. Khi lng LDL cao hn HDL th t l cholesterol trong mu s tng ln gy triu chng bnh tim mch nguy him.

H2/Pt
HO HO

CrO3
O

Zn/Hg, HCl

Cholesterol

Cholestanol

Cholestanon

Cholestan

2. ERGOSTEROL (C28H44O) - Tinh th, tnc= 163oC, []D= -130

HO

Ergosterol
R

- Ergosterol v cholesterol l nguyn liu sn xut vitamin D2 v D3.

R OH

Tin vitamin D

Ergosterol
HO

h
R

R CH2

HO HO

HO

Tachysterol

Lumisterol

Vitamin D2 (Ergocalciferol)

R OH

h
HO

Tin vitamin D
h h

7-Dehydrocholesterol
R R CH2

HO HO

HO

Vitamin D3 (Cholecalciferol)

Vitamin D4 : R =

3. STIGMASTEROL (C29H48O)
29 28 21 18 11 20 23 17 13 9 3 26 22 24 25 27

- Tinh th, tnc= 1700C, []D= -40.

19

1 15 7

- Trong du u nnh, tn ti di dng acetat.

HO

Stigmasterol
29 28 21 18 11 20 23 17 13 9 26 22 24 25 27

19

Sitosterol
HO

15 7

3 5

CC ACID MT
- C nhiu trong dch mt. - Khung gonan bo ha, cha nhiu nhm OH (3,6,7,11,12) hu ht c cu hnh . Ti C17 gn gc cha nhm COOH.
COOH
24

COOH
27

C24

C27

CC HORMON
Hormon l nhng cht do cc tuyn ni tit sinh ra, c tc dng gy nn cc phn ng sinh l khc nhau.
18 20

19

Khung Estran

Khung Androstan

Khung Pregnan

Estrogen

Androgen

Progestagen

1. Cc hormon sinh dc
@ Hormon sinh dc n : - ESTROGEN : iu ha cc chc phn ca c quan sinh dc v lm pht trin cc c quan ny giai on dy th.

Khung Estran
OH O OH OH HO HO HO HO OH

Estron

Estriol

17 -Estradiol

17-Estradiol

- PROGESTAGEN

Khung Pregnan

OH

HO

Progesteron

Pregnandiol

@ Hormon sinh dc nam:

Khung Androstan

HO

HO

Androsteron
O

5-iso-androsteron
OH

HO

Dehydro epi androsteron

Testosterol

2. Cc hormon tuyn thng thn

OH
21

O HO
11 1 3

X
17

X = H : Mineralocorticoid X = OH : Glucocorticoid

O
OH
CHO

HO

Cc mineralocorticoid c tc dng tng thi K+, H+, ti hp thu Na+ v gi nc.

Aldosteron

Cc Glucocorticoid tc ng ln s chuyn ha glucid, protid, lipid.

OH O HO
O OH O OH

Corticosteron
OH O HO OH

Cortison

Cortisol

GLYCOSID TIM
- La nhng glycosid steroid co tac dung ac biet len tim. - Vi lieu ieu tr co tac dung cng tim, ieu hoa nhp tim, vi qua lieu ieu tr th gay non, chay nc bot, lam ngng tim.

Dng a hoang hoa tm, Digitalis purpurea L. Ho Hoa mom soi Scrophulariaceae.

Truc ao, Nerium oleaner L. Ho Truc ao Apocynaceae

Bong bong, Calotropis gigantea (L.) Dryand ex.Ait. Ho Thien ly

Asclepiadaceae

CAU TRUC CUA GLYCOSID TIM

@ Cau truc phan ng:

CH2OH H H OH OH H OH O H H
OH OH

OH

OH CH3

OH

OH CH3

OH

OCH3

-D-Glucopyranose

-L-Rammose

-L-Oleandrose

Ngoai ra con gap cac ng D-fucose, ng thevetose. Trong cau truc cua ng co the mot nhom -OH b acetyl hoa.

Phan ng co the gom mot ng, nhng thong thng t 2-4 ng. Neu la nhieu ng trong o co glucose th glucose se ng v tr cuoi cung.

@ Cau truc phan aglycon:

Tat ca cac aglycon eu co nhan 4 vong chung cho cac hp chat steroid. Cac vong A & B: trans hay cis B & C: trans ; C & D: cis

@ Cau truc phan aglycon

14

OH
4 5

ng

- Thong thng co 2 nhom OH tai C3, C14, thng co cau hnh . - Mot vai trng hp co noi oi tai C4-C5; C11-C12. -Nhom OH con co mat tai C1, C5, C11, C12, C16. - Hai nhom OH gan nhau co the tao epoxy. - S oxi hoa c the hien bang s co mat cua mot ceton C12, hay mot epoxy C11, C12 hoac C7, C8.

LIEN QUAN GIA CAU TRUC VA HOAT TNH SINH HOC

O O

CH3 CH3 H3C H3C H3C HO OH HO O O HO O O O O OH

Digitoxin

- A & B: cis ; B & C: trans ; C & D: cis

ALCALOID
nh ngha - Ngun gc thc vt. - Thng cha Nitrogen trong vng d hon, c tnh base. - C c tnh dc lc hc liu lng thp. Phn loi - Alcaloid khng c nhn d vng. - Alcaloid c nhn d vng.

- Alcaloid c nhn sterol.

- Alcaloid c cu trc diterpen.

- Alcaloid l dn xut ca pyrol v pyrolidin. - Alcaloid l dn xut ca imidazol - Alcaloid l dn xut ca pyridin v piperidin - Alcaloid l dn xut ca tropan

- Alcaloid l dn xut ca quinolin

- Alcaloid l dn xut ca isoquinolin - Alcaloid l dn xut ca quinolizidin

- Alcaloid l dn xut ca quinazolin

- Alcaloid l dn xut ca acridin - Alcaloid l dn xut ca indol

- Alcaloid l dn xut ca purin

- Alcaloid l dn xut ca pyrolizidin - Alcaloid l dn xut ca phenantren

CC C TNH HA - L CA ALKALOID - a s alkaloid khng mu, kt tinh rn vi im nng chy xc nh, mt vi dng v nh hnh, mt vi dng lng (nicotin, coniin)
H
CH2CH2CH3 N H H
O

N N CH3

N OH OCH3

Coniin

Nicotin

Berberin

OCH3

- Alkaloid dng base t do hu nh khng tan trong nc, tan tt trong dung mi cloroform, dietyl eter. Cc mui ca alkaloid th tan trong nc, hu nh khng tan trong dung mi hu c nh cloroform, dietyl eter

- Da vo tnh base c trng ca cc alkaloid, c 2 phng php cn bn chit tch alkaloid ra khi bt cy kh:
@ Chit alkaloid bng dung mi hu c @ Chit alkaloid bng dung dch nc acid
COOCH3

H
N CH3

N N
O O N OH OCH3 OCH3

CH3

S CHIT ALKALOID BNG DUNG MI HU C

Bt cy kh
- Ha tan vo nc acid 2%, t0 - Lc

Dung dch
- Tn chit bng cloroform

- Base v c: NaOH hoc Ca(OH)2

Pha nc

Pha dung mi
- Lm bay hi di p sut km

Cc alkaloid th
- Sc k lp mng silica gel
- Sc k ct

Alkaloid 1

Alkaloid 2

Alkaloid 3

S CHIT ALKALOID BNG DUNG DCH NC ACID

Bt cy kh
- Tn chit vi metanol - Lc, thu hi dung mi

Cao metanol
- Ha vo acid acetic, un m - Chit vi cloroform

Dch cloroform

Dch nc
- C quay ui nc

Cao alkaloid th (dng acetat)

- Sc k lp mng silica gel

- Sc k ct

Alkaloid 1

Alkaloid 2

Alkaloid 3

Nang lc quay cc
Phan ln alcaloid co kha nang lam quay mat phang anh sang phan cc, v trong cau truc co carbon phi oi xng. a so ta trien.
Mot so khong co tac dung vi anh sang phan cc : piperin, papaverin.
MeO MeO N OMe

N O C CH CH CH CH

O O

Mot so alcaloid la hon hp racemic : atropin, atropamin...

H3C N H CH2OH

Piperin

Papaverin

OMe

O C CH O

Atropin

Nang lc quay cc la hang so giup kiem tra o tinh khiet cua alcaloid. Dang ta trien co hoat tnh sinh hoc manh hn dang hu trien va dang racemic.

Alcaloid l dn xut ca pyridin v piperidin

4

5 6

3 2

Ricinin C8H8O2N2
N H
OMe CN N Me O

N
1

Pyridin

Piperidin

NO2 Me K2Cr2O7 N O OMe NH3 - 33 0C N O CONH2 H2SO4

NO2 COOH MeONa N O Cl PCl5 POCl3 N CN Cl

OMe COOH MeOH N O OMe MeONa N CN OMe MeI ,P HCl

OMe COOMe N O OMe CN N Me O

-Nicotin c trong cy Thuc l Nicotiana tabacum L., Solanaceae.

N N CH3

- Nicotin l mt cht c, vi liu nh Nicotin kch thch h thn kinh trung ng, vi liu ln lm try tim mch, ngng h hp. - Nicotin c dng lm thuc tr su.

CH3 N
Picolin (2, 3 hoc 4-)

[O] KMnO4

COOH N
Acid pyridin carboxylic (2, 3 hoc 4-)

COOH N

Acid nicotinic (Niacin, acid 3-pyridin carboxylic) cha bnh bch tng. Amid ca n l vitamin PP.

CONHNH2

Isoniazid, Rimifon, cha bnh lao

N

@ Piperin (alcaloid ca ht tiu en)

N O C CH CH CH CH

O O

Piperin

HO CHCl3 HO NaOH R.T

HO HO

CHO

CH2I2 NaOH

O O

CHO

Catechol
CH3CHO NaOH O O CH CH CHO Ac2O AcONa CH CH CH CH COCl O N O C O C6H6 CH CH CH CH O O O CH CH CH CH COOH

PCl5

HN

Piperin

Bot tieu en (10g)

- Trch nong vi ru etylic 95%, 2h - Loc

Ba

Dch alcol
- Co quay thu hoi dung moi - Them dung dch KOH/alcol 10% (10 ml) - e lang (loai phan khong tan)

Piperin

Khong 25 loi, chia thnh 2 nhm ty theo c cu.

Cy phin (anh tc)

@ Alcaloid c nhn isoquinolin

MeO MeO N MeO OMe OMe MeO N Me OMe OMe MeO N Me OH OMe

MeO

Papaverin

Laudanosin

Laudanin

@ Alcaloid thuc nhm phenantren

HO
4 2 3 1 11 10 12 13 14 5 15 16 8 7 9

MeO
4

2 3 1 11 10 12 13 14 5 15 16 8 7 9

MeO
4

2 3 1 11 10 12 13 14 5 15 16 8 7 9

N CH3
HO

N CH3
MeO

N CH3

HO

Morphin C17H19O3N

Codein C18H21O3N

Thebain C19H21O3N

Morphin [Morphinan-3,6-diol-7,8-didehydro-4,5-epoxy-17-metil (5, 6)]

Tinh th hnh lng tr, khng mu, c v ng. Tan trong benzen, cloroform, eter du ha, khng tan trong aceton. Trong y hc, morphin dng lm thuc gim au trong cc trng hp au d di nh cc chng au do ung th, au do si thn, si mt. Codein dng cha ho.

HO
4

2 3 1 11 10 12 13 14 5 15 16 8 7 9

HO

O N CH3
13 5 14 6

H N CH3

HO H

HO

Morphin [Morphinan-3,6-diol-7,8-didehydro-4,5-epoxy-17-metil (5, 6)]

Xac nh cau hnh tuyet oi cua cac carbon phi oi xng (C5, C6, C9, C13, C14)?

HO
4

2 3 1

CH3
11 10

C O O
4

2 3 1 11 10 12 13 14 5 15 16 8 7 9

O
5

12 13 14 15 16 8 7 9

N CH3

CH3COOH bng CH3

N CH3

HO

C O O

Morphin

Heroin

Methadone
O N