Baigiang

Ni dung chnh
1 Hp cht tp chc
Bi ging
Ha hu c II
Ts. Nguyn Th Thu Trm
B mn: Ha hc - Khoa KHCB
Email: ntttram@ctump.edu.vn
1.1 Halogenoacid
1.2 Hydroxyacid
1.3 Hp cht c nhm chc carbonyl
1.4 Carbohydrat
1.5 Acid amin, peptid v protid
1.6 Lipid
2 Hp cht d vng
2.1 Hp cht d vng 5 cnh 1 d t
2.4 Hp cht d vng 7 cnh
2.5 Hp cht d vng ngng t
3 Hp cht thin nhin
Cn Th, 2015
3.1 Acid nucleic

3.2 Terpen
3.3 Steroid
Ti liu tham kho

1 L Ngc Thch, Ha hc hu c (cc nhm nh chc chnh); NXB HQG TP.HCM, 2002
2 L Ngc Thch, Bi tp Ha hc hu c (cc nhm nh chc chnh); NXB HQG
TP.HCM, 2013
3 Nguyn Kim Phi Phng, Ha hu c, Bi tp Bi gii; NXB HQG TP.HCM, 2006
4 Phan An, Ha v c v hu c; NXB Y Hc, 2007
5 Trn Mnh Bnh, Nguyn Quang t, Ha hc hu c, tp 1; NXB Y Hc, 2007
6 Trn Mnh Bnh, Nguyn Quang t, Ha hc hu c, tp 2; NXB Y Hc, 2007
7 Trng Th K, Ha hu c, Hp cht hu c n chc v a chc, tp 2; NXB Y Hc,
2009
8 L Vn ng, Chuyn mt s hp cht thin nhin; NXB HQG TP.HCM, 2005
9 Herbert M., Howard N., Jacob S., Geogre J.H., Theory and problems of organic chemistry,
3rd edition; McGraw-Hill, 1999
10 Jean Bruneton, Pharmacognosie Phytochimie plantes mdicinales; Lavoisier, 2009
2
1.1 Hp cht tp chc- Halogenoacid
1.1.1 Danh php

Tn quc t (IUPAC)
Tn thng thng
Acid 2-clorobutanoic
Acid -clorobutiric
Acid -cloro--metylvaleric
Acid 2-cloro-3-metylpentanoic
?
COOH
HCOOH
Acid formic
CH3COOH
Acid acetic
CH3CH2COOH
Acid propionic
CH3(CH2)2COOH
Acid butiric
CH3(CH2)3COOH
Acid valeric
CH3(CH2)4COOH
Acid caproic
..
COOH
Cl
COOH
Br
COOH
COOH
Br
Br
Br
VD1: Gi tn cc hp cht sau theo danh php quc t:
VD2: Vit cu trc ha hc ca cc hp cht sau:

a. Acid 2,3-dimetil-2,4-dicloroheptanoic
b. Acid cis-1,2-ciclohexandicarboxilic
c. Acid trans-1,2-ciclopentandicarboxilic
d. Acid 2,3-dibromobutandioic
4
1.1.2 Phng php iu ch

Halogen ha acid carboxylic
Cl2
H+, P
CH3 CH COOH
HCl
(sn phm chnh)
HCl
(sn phm chnh)
Cl
CH3 CH2 COOH

Cl2
as
CH2 CH2 COOH

Cl
COOH
COOH
Cl2
AlCl3
HCl
Cl
Cng HX vo acid cha no

CH2 CH COOH
HCl
CH2 CH2 COOH

Cl
5
1.1.3 Tnh cht ha hc

Phn ng thy phn
R CH COOH
HO-
R CH COOH
(C CHE PHAN NG)
OH
C
O
Br (CH2)5 COOH
H2O, Ag2O
HO
Cl
CH2
CH2 CH2 COOH
-Caprolacton
(6-Hexanolid)
(CH2)5 COOH
O
H2O, Ag2O
(4-Butanolid)
Phn ng kh
CH3 CH CH2 COOH
Cl
KOH/alcol
-Butirolacton
CH3 CH CH COOK
6
Nu
Nu
HO
HO-
_ H+
O
C
_ X
O
C
Nu
(S)
HO
O
HO
C
O
H+
C
H
OH
R
(S)
C
H
7
OH
1.1.4 ng dng
Tinh th,
Monocloroacetic MCA (ClCH2COOH)
tnc = 63oC,
D tan trong nc, etanol
(CH3CO)2O, H2SO4
Cl2
CH3COOH
ClCH2COOH
HCl
hoc
Cl
Cl
C
2 H2O,
Cl
H2SO4
o
ClCH2COOH
HCl
Dng tng hp acid malonic, ester malonat, cht mu...
H3O+
ClCH2COO-Na+
CN
NC
HOOC
CH2 COOH
Acid malonic
CH2 COOEtOH, H+
8
EtOOC CH2 COOEt

Dietylmalonat
Dicloroacetic DCA (Cl2CHCOOH)

iu ch:
Cl3CCH(OH)2
CaCO3, NaCN
(Cl2CHCOO)2Ca
H+
Cl2CH2COOH
hoc
Cl
Cl
C C
Cl
Cl
2H2O
to
Cl2CH2COOH
2 HCl
Preliminary studies: DCA can slow the growth of certain tumors in animal
studies and in vitro studies.
However, no support the use of DCA for cancer treatment at this time.
Tricloroacetic TCA (Cl3CCOOH)

Cl3CCH(OH)2
Cl3CCOOH
HNO3
H2O
to
Cl3CCOOH
Cl3CH
CO2
- Precipitation of macromolecules: proteins, DNA, and RNA.

- Solutions containing TCA as an ingredient are used for cosmetic treatments:
chemical peels, tattoo removal, the treatment of warts
9
1. Hy sp xp cc cht sau theo th t tnh acid tng dn

a.CH3CH2COOH, FCH2COOH, BrCH2COOH
b. Acid p-bromobenzoic, acid p-nitrobenzoic, acid 2,4-dinitrobenzoic
2. ngh phng php bin i cc hp cht sau
a. Bromobenzen thnh acid benzenoic
b. CH3CH2CH2Br thnh CH3CH2CH2COOH
c. HOCH2CH2CH2Cl thnh HOCH2CH2CH2COOH
d. t-BuCl thnh t-BuCOOH
3. Mt tng hp ibuprofen c gii thiu di y: ngh c cu
cc hp cht trung gian t A n D
10
Ibuprofen
1.2 Hp cht tp chc- Hydroxyacid
1.2.1 Danh php

Tn quc t (IUPAC)
Tn thng thng
Acid -hydroxybutiric
Acid 2-hydroxybutanoic
Acid 2-metil-4-hydroxypentanoic
CH3 CH CH2 CH COOH

OH
Acid -etil--hydroxyvaleric
CH3
COOH
Acid 2-hydroxybenzoic
OH
Acid salicilic
11
1.2.2 Phng php iu ch

Thy phn halogenoacid
H2O
Hon nguyn
T aldehyd-ceton (iu ch -hidroxycarboxilic)
VD:
C6H5 C CH2 CH3

O
HCN
H3O+
12
Phn ng Reformatski (iu ch -hidroxycarboxilic)
CH3
VD:
CH3CH2CCH2COOH
OH
CH3CHCH2COOH
OH
T cc hp cht etylen oxid (iu ch -hidroxycarboxilic)
T acid amin
13
iu ch phenolacid
Acid p-hydroxybenzoic
Acid salicilic
(Acid o-hydroxybenzoic)
T acid amin
iu ch phenolacid
Acid p-hydroxybenzoic
Acid salicilic
(Acid o-hydroxybenzoic)
14
1.2.3 Tnh cht ha hc

Phn ng tch nc
- Vi -hydroxyacid
O
HO
OH
CH
CH
R
R HC
OH
HO
CH R
2 H2 O
Lactid
- Vi -hydroxyacid
R CHOH CH2 COOH
R CH CH COOH
H 2O
- Vi , -hydroxyacid
CH2
H2C
CH2
CH2
C
OH HO
CH2
H2C
CH2
HO
OH
hoc H+
CH2
H2C
C O
H2C
hoc H+
H2O
CH2
CH2
H2C
CH2
H2O
C O
O
15

Cc vng lacton c vai tr quan trng trong mt s dc phm
Bot la kho
Chiet bang hexan
Dch chiet
Artemisia annua L.
Thanh hao hoa
vang
O
CH3
Co quay thu hoi dung moi
Cao hexan (cha Artemisinin tren 80%)
O
O
H
C
O
H
H
CH3
Artemisinin cha st rt
- Tinh th hnh kim, mu
trng, khng mi, v hi
ng.
-
t tan trong nc, etanol;

tan nhiu trong hexan, ete
du ha, cloroform, v
axeton.
Ket tinh sau 24-48h
Artemisinin tho
- Ket tinh lai trong etanol
nong
- Tay mau bang than hoa

tnh
Artemisinin tinh khiet

16
Humans, guinea pigs, some

monkeys and many birds.
Aspergillus fumigatus
Aflatoxin
17
Cc phn ng khc ca alcolacid

- Phn ng ca chc COOH (tnh acid, to ester)
- Phn ng ca chc OH (to ester vi dn xut acid, phn ng th)
Metyl salicilat
Aspirin (acid acetylsalicilic)

18
1.2.4 ng dng mt s alcolacid ph bin

Acid Glycolic
HOCH2COOH
- Chit xut t cy ma, c ci ng.

- Tinh th khng mu, khng mi, ht m cao.
ng dng:
- Acid glycolic 50% lm tng s hp thu ca thuc t dng
bi qua da.
- Gip loi b vt thm nhanh hn, ngn nga hot ng ca
tyrosinase, kch thch ti to t bo da.
19
Acid Lactic CH3CHOHCOOH

- Trong dc phm: khng khun, thuc tr ri lon tiu ha, gip
ng rut khe mnh,
- Trong cng ngh thc phm: ln men lactic lm sa chua, ph mai
- Trong m phm: gi m cho da, ty t bo cht
Acid p-hidroxybenzoic
Acid p-hidroxybenzoic
R : -CH3
Nipagin
R: -nC3H7 Nipazol
20
1.3 Hp cht hai chc c nhm carbonyl
1.3.1 Hydroxy aldehyd v hydroxy ceton

iu ch
2 CH3CH2CH2C OC2H5
4 Na
- 2 C2H5ONa
ONa
CH3CH2CH2C
CCH2CH2CH3
ONa
H2O
O
CH3CH2CH2C
CHCH2CH2CH3
OH
CH2 CH2
O
HOCH2CH2OH
CH3CCH2CH2COCH2CH3
H+
CH3
CH2CH2COCH2CH3
1.LiAlH4
+
2.H3O
O
CH3CCH2CH2CH2OH
HOCH2CH2OH
H 3O +
CH2 CH2
O
CH3
21
O
CH2CH2CH2OH
Tnh cht ha hc
Phn ng loi nc
H+
R CH CH2 CHO
hoc OH
OH
R CH2 C
CH2 CH CH2 R'
+ H2 O
R CH CH CHO
-
H+
hoc OH
OH
R CH2 C
+ H2O
Phn ng oxy ha
CH3 C
CH CH3
CH3
HIO4
O OH
CH CH CH2 R'
C OH
CH3CHO
Phn ng to bn acetal v bn cetal vng

H
HOCH2CH2CH2CHO
O
OH
CH3
HOCH2CH2CH2CH2CCH3
O
Bn acetal vng
OH
Bn cetal vng
22
HIO3
Cc bn acetal vng l nhng cht trung gian tng hp nhiu hp cht

hu c.
NaBH4
H
O
OH
HOCH2CH2CH2CH2CH2OH
1.CH3MgBr
+
2. H3O
HOCH2CH2CH2CH2CHCH3
OH
CH3COCl
H
O
OCOCH3
H2Cr2O7
O
VD: Hy ch ra nhm OH bn acetal ca -D-Glucopyranose, ng thi vit sn phm to

thnh khi cho -D-Glucopyranose tc dng vi:
a. NaBH4
CH2OH
b. CH3OH, H+
H
H
OH
OH
OH
OH
-D-Glucopyranose
23
1.3.2 Ceto-aldehyd, ceto-acid, ceto-ester

R C
(CH2)n
R C
CHO
(CH2)n COOH
R C
O
Ceto-acid
O
Ceto-aldehyd
(CH2)n COOR'
O
Ceto-ester
iu ch
Oxi ha trc tip
Ngng t Claisen
O
O
HCOOC2H5
NaOC2H5
C2H5OH
NaOC2H5
CH3 C OC2H5
CHO
H3O+
H3O+
CH3 C
O
C ch:
CH2COOC2H5
O
O
EtO-
CH OEt
H C OEt
O
CHO
EtO-
O
CHO
H+
CHO
24

O
COEt
O
+
PhCOOEt
CH3COEt
CH3COPh
Base
H+
Base
H+
CH2COEt
PhCOCH2COPh
ether
O
EtONa, Etanol
ether
O
OEt
O
C OEt
H3O+
O
OEt
O
OEt
EtONa, Etanol
H3O+
O
C OEt
OEt
25
Tnh cht ha hc
Cn bng ceton- enol
O
CH3 C
H
CH3
CH3 C
CH2
Ceton
CH
CH3
Enol
Dung dch nc
84%
16%
Dung dch hexan
8%
92%
Tnh acid ca hp cht c 2 nhm carbonyl

O
H+
CH2
O
CH
..
O
CH3CCH2CCH3
>
CH
CH3CCH2COCH3
>
CH
CH3CCHCCH3
CH3
>
NCCH2CN
26
>
CH3OCCH2COCH3
Chuyn v benzylic
C6H5 C C
C6H 5
KOH
C6H5
HO
O O
C C
C6H 5
O OH
Benzil
Benzilic acid
C ch
R C
R'
HO
OH
R C
O O
R'
HO
O O
R
O C
O O
R'
O O
R
H+
O C
R'
OH OH
27
R'
Phn ng decarboxyl
O
CH3CH2CH2CCHCOOH
CH3CH2CH2CCH2CH2CH3
CO2
CH2CH3
Phn ng t sc hp
O
O
C
COOEt
CH3CH2COCH2CH2COOEt
EtONa
EtONa
H+
H+
O
O
CH3
28
1. Heptanal + Bromoacetat etyl + Zn, roi H2O

C11H22O3)
A + CrO3
B + Etoxid natri, roi Clorua benzil
C
C + HO-, un nong; roi H+, un am
C15H2.
22O)
Bromur alil + Mg E (C H )
6
10
E + HBr F
F (lng tha) + Ester malonic natri G
(C13H23O4Br)
G + Etoxid natri H
H + (HO-, un nong); ri (H+, un nong) I
(C8H14O2)
3. 1-Heptin + LiNH2 J
J + 1-Cloro-3-bromopropan K (C10H17Cl)
K + Mg, ri CH3(CH2)9CHO; sau o H29+ L
A
B
D
1.4 C
Phn loi :
arbohydrat
C 3 loi carbohydrat
Monosacarid: cn gi l ng n, khng b thy phn.
CH2OH
H
O
H
OH
OH
OH
CH2OH
O
HO
CH2OH
OH
-D-Glucopyranose
OH
OH
-D-Fructofuranose
Oligosacarid: do cc monosacarid kt hp li vi nhau bng lin kt

glycosid , khi b thy phn cho mt vi (oligo: mt vi) monosacarid. Trong
quan trng nht l disacarid.
Saccarose
Polysacarid: do hng trm n hng nghn monosacarid kt hp li vi

nhau bng lin kt glycosid.
30
Amylose
1.4 C
1.4.1 Monosacarid
1.4.1.1 Danh php
Tn gi theo s cacbon, chc aldehyd hoc ceton
Monosacarid c cha chc aldedyd gi l aldose
Monosacarid c cha chc ceton gi l cetose
Nu s C trong phn t l: 3 th gi l triose
4 th gi l tetrose
5 th gi l pentose
6 th gi l hexose
CH2OH
CHO
C O
CHOH
CHOH
CHOH
CHOH
CH2OH
Cetohexose
CHOH
Aldopentose
CHOH
CH2OH
31
arbohydra
1.4 C
arbohydra
Danh php D/L : c s dng rng ri khi gi tn carbohyrat

CHO
H
CHO
OH
CH2OH
D-Aldehyd glyceric
CHO
H
OH
HO
CH2OH
L-Aldehyd glyceric
CHO
HO
CH2OH
HO
OH
HO
HO
H
H
OH
OH
H
H
CH2OH
D-Galactose
HO
O
H
CH2OH
H
O
OH
OH
HO
OH
HO
CH2OH
CH2OH
L-Galactose
D-Fructose
32
CH2OH
L-Fructose
1.4 C
arbohydra
Danh php R,S : mc d ch r cu hnh tng cacbon th tnh nhng

danh php ny t c s dng khi gi tn carbohydrat
1CHO
H
HO
H
H
1CH2OH
OH
H
HO
OH
2C
H C OH
OH
CH2OH
CH2OH
(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanal
(3S,4R)-1,3,4,5-Tetrahydroxy-2-pentanon
Gi tn theo vng:
VD: Glucopyranose (vng 6 cnh)
O
O
Pyran
Furan
Fructopyranose (vng 6 cnh)

Glucofuranose (vng 5 cnh)
Fructofuranose (vng 5 cnh)
33
1.4 C
6
CH2OH
CH2OH
HO
H
OH
OH
-DGalactopyranose
CH2OH
CH2OH
O
H
OH
OH
HO
OH
OH
-DGalactopyranose
CH2OH
O
OH
HO
HO
CH2OH
OH
OH
OH
-DFructofuranose
-DFructofuranose
CH2OH
O
H
OH
OH
OH
O CH2OH
HO
H
OH
-DGlucopyranose
OH
OH
OH
-D34
Fructopyranose
arbohydra
1.4 C
1.4.1.2 Mt s kiu trnh by monosacarid
arbohydra
Theo cng thc chiu Fischer

CHO
CH2OH
H C OH
HO
HO
O
H
H C OH
OH
H C OH
OH
CH2OH
CH2OH
D-Gluco
D-Fructo
Theo cng thc chiu Haworth

CH2OH
H
CH2OH
O
H
OH
OH
H
H
OH
OH
-D-Glucopyranose
O
H
OH
OH
OH
-D-Glucopyranose
OH
HO
OH
H
H
CH2OH
O
HO
OH
CH2OH
CH2OH
O
CH2OH
OH
OH
-D-Fructofuranose
35
-D-Fructofuranose
1.4 C
Cch ng vng to bn acetal vng
36
arbohydra
1.4 C
37
arbohydra
1.4 C
Theo cng thc chiu Reeves
CH2OH
O
H
OH
HO
OH
OH
H
OH
H
H
OH
H
OH
OH
CH2OH
HO
OH
OH
CH2OH
O
HO
OH
CH2OH
HO
H
OH
OH
H
38
arbohydrat
O
2
1.4 C
O
3
C1
C4
HO
OH
HO
OH
O
HO
OH
OH
OH
OH
-D-Glucopyranose
OH
OH
O
OH
-D-Idopyranose
OH
OH
HO
OH
-D-Glucopyranose
HO
OH
O
O
HO
OH
OH
-D-Glucopyranose
OH HO
OH
OH
OH
OH
OH
-D-Glucopyranose
HO
OH
OH
HO
HO
arbohydrat
OH
OH
OH
O
HO
HO
OH
OH
-D-Idopyranose
-D-Idopyranose
-D-Idopyranose
39
1.4 C
arbohydrat
Cu trng u i
H
CH2OH
HO
HO
HO
OH
+ 19
CH2OH
HO
HO
H
H
OH a
OH
-D-Glucopyranose (64%)
-D-Glucopyranose (36%)
+ 52,70
HO
OH e
H
CH2OH
+ 1120
CHO
O
H C OH
OH
OH
H
HO
H C OH
CH2OH
HO
HO
H
H C OH
CH2OH
40
H
OH
OH
1.4 C
1.4.1.3 Tnh cht ha hc
Phn ng ca nhm aldehyd (ceton)
CH2OH
HO
Phn bit ng kh v ng khng

kh.
Phn ng oxi ha
HO
H
O
OH
OH
arbohydrat
HO
HO
H
ng kh
CH2OH
OR
OH
H
ng khng kh
Tt c ng kh s tham gia phn ng vi thuc th Tollens (AgNO3 trong nc

NH3), thuc th Fehling (CuSO4 trong tartrat natri), thuc th Benedict (CuSO4 trong
citrat natri).
COOH
CH2OH
HO
HO
H C OH
OH
HO
Cu(OH)2
Cu2O
2 H2O
H C OH
OH
H C OH
CH2OH
-D-Glucose
H
CH2OH
HO
HO
H
COOH
H C OH
OH
OH
H
2 Ag
H2O
HO C
H C OH
H C OH
CH2OH
41
2 Ag
1.4 C
Phn ng kh
H
CH2OH
CHO
CH2OH
HO
HO
H
H C OH
OH
HO
H C OH
OH
H
H C OH
1.NaBH4
2. H2O
H C OH
CH2OH
-D-Glucopyranose
arbohydrat
HO
H C OH
H C OH
CH2OH
D-Glucitol (D-Sorbitol)
S to thnh osazon
H
C
CHOH
(CHOH)n
C N NH C6H5
3 C6H5 NH
NH2
C6H5NH2
(CHOH)n
CH2OH
Aldose
C N NH C6H5
NH3
Glucosazon
CH2OH
Phenylhydrazin
Phenylosazon
Maltosazon
Cc osazon ca cc loi ng khc nhau s kt tinh cho ra

tinh th khc nhau nn c th s dng dn xut ny xc
nh phn ln cc loi ng.
42
Galactosazon
Lactosazon
H2O
1.4 C
C ch to thnh osazon
H
CHOH
C O
(CHOH)n
C6H5 NH NH2
arbohydrat
(CHOH)n
NH3
C6H5NH2
CH2OH
CH2OH
OH
H2N NH C6H5
NHNHC6H5
NH2NHC6H5
H3O+
H
C6H5 NH
C6H5 NH
N
C
H O H
N
C
OH2
_ HO
2
C
NHNHC6H5
43
H2O
1.4 C
Phn ng tng mch carbon

CN
H
OH
CHO
HO
OH
OH
OH
OH
OH
H+
OH
H2O OH
H
OH
OH
OH
OH
H2O
H+
HO
OH
H
OH
Na(Hg) OH
CO2
H
OH
OH
CH2OH
CHO
HO
OH
H2O
Na(Hg)
OH
OH
OH
CO2
HO
OH
OH
OH
CH2OH
CH2OH
CH2OH
CH2OH
OH
O C
COOH
HO
OH
CH2OH
CH2OH
CN
CH2OH
OH
H2O
CH2OH
HCN
CHO
O C
COOH
OH
arbohydrat
Phn ng gim mch carbon

CHO
H
OH
OH
H
OH
OH
CH2OH
COO
COOH
H
Br2
H 2O
OH
OH
H
CaCO3
OH
OH
H
OH
OH
OH
OH
CH2OH
CHO
CH2OH
HO
Ca
H2O2
3+
Fe
OH
OH
CH2OH
44
1.4 C
Phn ng ca nhm -OH
arbohydrat
Phn ng to ester
H
CH2OH
HO
HO
(CH3CO)2O
H
OH
OH
H3COCO
Piridin, 0 C
0
H3COCO
CH2OCOCH3
OCOCH3
OCOCH3
H
-D-Glucopyranose
Penta-O-acetil--D-glucopyranose
Phn ng to eter
H
CH2OH
HO
HO
OH
OH
H
Ag2O
CH3I
CH2OCH3
CH3O
CH3O
H
H
OCH3
OCH3
-D-Glucopyranose
45
1.4 C
Phn ng to glycosid
arbohydrat
Glycosid khi b thy phn s to ra phn ng v phn aglycon

VD:
Lin kt glycosid
H
CH2OH
HO
HO
OH
p-Hydroxyphenyl -D-glucopyranosid
HO
H
Phn ng
Phn aglycon
Cch gi tn glycosid:
Tn nhm alkil + tn ng (thay ose thnh osid)
CH2OH
O
O CH3
CH2OH
HO
HO
CH2OH
OH
Metyl -D-fructofuranosid
HO
CH2OH
O
HO
O-Hydroxymetylphenyl -D-glucopyranosid
46
1.4 C
arbohydrat
Mt vi VD v glycosid
OH
OH
OH
OH
HO
HO
OH OH
H
HO
OH
HO
HO
O OH O
OH H
OOH O
OH H
3-O--D-Galactopyranosyl
quercitin
3-O--D-Glucopyranosyl
quercitin
29
28
22
21
19
23
12
11
18
H
4'
HO
HO
6'
5'
3'
OH
OH
1'
25
HO
10
14
OH
C=C
H3CO
15
HO
OH
7
4
26
16
27
H O
2'
17
13
24
20
OH
3-O- -D-Glucopyranosylstigmasterol
HO
OH
HO
HO
O
OH
Kaempferol 3-O-{6-[(6-O-E-feruloil)--D-galactopiranosi
-D-glucopiranosid}
47
Phn ng to phc mu xanh vi

Cu(OH)2
H
H
CH2OH
HO
1.4 C
HO
HO
OH
OH
Cu(OH)2
HO
H
O
Cu
CH2OH
O
H
HOCH2 H
arbohydrat
OH
OH
Phc ng mu xanh
Phn ng ln men
Ln men ru
Ln men lactic
C6H12O6
D-Glucose
Ln men citric
Ln men butyric
Ln men
aceton-butylic
2 C2H5OH
2 CO2
CH3CHOHCO2H
COOH
HOOCCH2CCH2COOH
OH
CH3CH2CH2CO2H
CH3COCH3
H 2O
+ 2CO2
C4H9OH
+ 2H 2
C2H5OH
48
+ 3 CO2 +
H2
1.4 C
1.4.2 Disacarid C12H22O11
arbohydrat
C th chia disacarid ra lm 2 loi: ng kh v ng khng kh

ng kh: Maltose, cellobiose, lactose
Maltose hay 4-O-(-D-Glucopyranosyl)-D-glucopyranosid
H
CH2OH
HO
HO
OH
CH2OH
HO
CH2OH
HO
HO
CH2OH
HO
OH
OH
OH
4-O-(-D-Glucopyranosyl)--D-glucopyranosid
H
OH
OH
Lactose hay 4-O-(-D-Galactopyranosyl)-D-glucopyranosid

OH
CH2OH
H
HO
H
H
OH
CH2OH
O
OH
Cellobiose
HO
H
CH2OH
H
HO
OH
OH
H
CH2OH
HO
HO
H
H
1
CH2OH
H
H
HO
HO
CH2OH
O
OH
O
OH
H
OH
OH
OH
OH
H
49
1.4 C
arbohydrat
ng khng kh: Saccarose (ng ma) C12H22O11

H
CH2OH
HO
HO
O
1
2
3
HO
Ni - glucosid
CH2OH
H
O
HO
2 H
3
HO
Ni - fructosid
H
6
CH2OH
2-O- (-D-Glucopyranosyl)--D-fructofuranosid
Nng lc trin quang [] = + 66,50

1 mol saccarose b thy phn cho ra 1 mol D-glucose v 1 mol D-fructose.
S thy phn ny lm thay i gc quay cc ban u ca saccarose, t (+)
chuyn thnh (-). Hin tng ny gi l s nghch quay.
[]D-glucose= + 52,70 []D-fructose= -92,40
Kt qu l dung dch saccarose sau khi thy phn c gc quay cc m.
50
1.4 C
arbohydrat
1. Trnh bay cong thc Haworth va cau trang u ai

cua cac ng co ten goi nh sau
a. 6-(O--D-Galactopyranosyl)-D-galactopyranosid
b. 4-(O--D-Mannopyranosyl)--D-fructofuranosid
c. -D-Galactopyranosyl (16)--D-glucopyranosyl (1 2)--D-fructofuranosid
d. -D-Glucopyranosyl (16)--D-glucopyranosyl (1 2)--Dfructofuranosid
i ten cac ng theo danh phap IUPAC

OH
OH
OH
O
HO
O
O
OH
OH
OH
HO
OH
O
HO
HO
O
HO
HO
OH
HO
OH
CH2OH
O
OH
HO
CH2OH
OH
51
OH
1.4 C
arbohydrat
3. Gentiobiose, thuc loi ng kh, l mt disaccarid him. Khi thy gii

bi dung dch nc acid, Gentiobiose ch cho ra D-glucose. Cho Gentiobiose
tc dng vi CH3I/Ag2O cho dn xut octametyl, cht ny khi b thy gii bi
dung dch nc acid, s cho mt mol 2,3,4,6-tetra-O-metyl-D-glucopyranose
v mt mol 2,3,4-tri-O-metyl-D-glucopyranose. Bit rng Gentiobiose c cha
mt ni -glycosid. V cu trc ca Gentiobiose (trnh by bng cu trng
gh) v gi tn Gentiobiose theo danh php quc t.
4. Trehalose la mot disaccarid, co lap c t nam

men, con trungTrehalose thuoc loai ng khong
kh, khi b thuy giai bi dung dch nc acid se cho 2
mol D-Glucose. Trehalose b thuy giai bi enzym glucosidase ma khong b thuy giai bi enzym glucosidase. Ve cau truc cua Trehalose (trnh bay bang
cau trang ghe) va goi ten Trehalose theo danh phap
quoc te.
52
1.4 C
arbohydrat
5. Melibiose la mot disacarid. Co the biet c cau truc

cua Melibiose nh vao cac ket qua sau:
a) Melibiose la ng kh, co kha nang lam thay oi
tnh quay quang, co the thanh lap phenylosazon.
b) Khi thuy giai vi acid hoac vi -galactosidase,
Melibiose cho ra D-galactose va D-glucose.
c) Metyl hoa va thuy giai Melibiose cho 2,3,4,6-Otetrametyl-D-galactose va 2,3,4-O-trimetyl-D-glucose.
Giai thch va cho biet cau truc cua nhng san pham
trong tng phan ng t a...c. Cho biet cau truc cua
Melibiose va goi ten danh phap quoc te cua hp chat
nay. (Trnh bay tat ca cong thc di cau trang ghe).
53
1.4 C
arbohydrat
1.4.3 Polysacarid
- Polysacarid l nhng hp cht bao gm hng trm n hng nghn gc
monosacarid kt hp vi nhau bng lin kt glycosid.
- Polysacarid khng phi l ng kh v khng lm thay i tnh quay
quang.
- Polysacarid quan trng v hay gp l tinh bt, cellulose v glycogen.
CTTQ: (C6H10O5)n
54
1.4 C
1.4.3.1 Tinh bt
Tinh bt c 20% amylose v 80% amylopectin
Cu trc ca amylose
4
1
1,4-(-D-Glucopyranosid)
55
arbohydrat
1.4 C
Cu trc ca amylopectin
arbohydrat
ng dng:
- Tinh bt c s dng lm t dc.

- Sn xut giy, keo dn h, x l nc.
- Cch c th ngi tiu ha tinh bt: nc bt v bao t c enzym
glycosidase s thy gii ni -glycosid cho ra cc phn t glucose.
56
1.4 C
1.4.3.2 Cellulose
Lin kt Hydrogen
Cy bng vi
Cy ay
ng dng:
- Lm pha tnh trong sc k ct.
- Ester ca cellulose:
Nitrat cellulose: cht n, verni sn.
Acetat cellulose: tm phim, giy lc, si t
tng hp
- Eter ca cellulose: metil, etil, propildng
lm cht n nh, cht kt dnh, sn phm
ty trang.
- Cacboximetilcellulose (CMC) : t dc,
thnh phn ca thc phm n king
57
arbohydrat
1.4 C
1.4.3.3 Glycogen
arbohydrat
- D tr nng lng (ngi, ng vt, nm), iu ha lng glucose

mc cn thit cho c th.
- Tch ly gan vi t l 20%
58
1.4 C
1.4.3.4 Chitin
ng dung
Bao quan trai cay
Lam lp boc ao ben ngoai
vien thuoc
Ha cholesterol trong mau
1.4.3.5 Pectin
59
arbohydrat
1.5.1 Acid amin (amino acid)
CH COOH
H2N
R
Trong gc R
- Alkyl (mch h hoc nhnh)
- Cycloalkyl, Ar-, gc d vng
- Cha hoc khng cha mt s nhm chc (-SH, -OH)
Xem Bng 29.1 (trang 63) : 20 acid amin ph bin.
H2N
H2N
CH2 CH2 CH2 COOH
Acid 4-aminobutanoic
Acid -aminobutyric
CH3 CH
CH COOH
COOH
CH3 NH2
Acid 2-amino-3-metylbutanoic
Acid -amino- -metylbutyric
Acid 3-aminobenzoic
Acid m-aminobenzoic
60
Trong thin nhin cc acid amin c cu hnh L

COOH
H2N
H
R
L-Aminoacid
Acid amin c dng ion lng cc
H3N
CH COO
R
H3N
CH COOH
R
Dng cation
H 3 O+
H3 N
CH COO
HO-
H2 N
Ion lng cc
CH COO
Dng anion
Acid amin hin din ch yu dng no trong 3 dng trn l ty thuc

vo pH ca mi trng. pH trung gian th acid amin dng ion lng
cc (gi tr pH ny gi l im ng in pI ). Xem Bng 29.2.
61
Da vo s khc nhau v im ng in, ngi ta c th tch hn

hp acid amin thnh cc cu t ring bit bng phng php in di
VD: Tch hn hp 3 acid amin : lysin (tnh kim), alanin (trung tnh),
acid aspartic (tnh acid)
H2N
CH2CH2CH2CH2 CH COOH
Lysin, pI = 9,74
NH2
CH3 CH COOH
Alanin, pI = 6,00
NH2
HOOC
CH2CH2 CH COOH
Acid aspartic, pI = 2,77
NH2
62

Tm giy trc khi in di
pH =6,00
Tm giy sau khi in di
CH3 CH COO
NH3
OOC CH2CH2 CH COO

NH2
H 3N
CH2CH2CH2CH2 CH COOH
NH3
63
1.5.1.1 Tng hp acid amin

- T -halogenoacid
CH3 CH CH2 CH2 COOH
CH3
1. Br2,
2.
PBr3
H2O
CH3 CH CH2 CH COOH

CH3
NH3
CH3 CH CH2 CH COOH
lng tha
Br
CH3CHO
CH3
NH2
Leucin (45%)
- Tng hp Strecker
NH3, HCN
CH3
H3 O+
CH CN
CH3 CH COOH
NH2
Alanin
NH2
- T ester malonat
CH2(COOEt)2
NaOEt
i_C4H9_Br
EtOH
i_C4H9_CH(COOEt)2
Br2
CCl4
i_C4H9_CH2COOH
Br2
i_C4H9CHBrCOOH
NH3
- Tng hp Gabriel
CH2(COOEt)2
HCl
N K
O
CHBr(COOEt)2
i_C4H9CHNH2COOH
O
N CH(COOEt)2
EtOAr X
O
O
Ar
CH COOH
NH2
H3O+
t
N C (COOEt)2
64 Ar
O
1.5.1.2 Tnh cht ha hc ca acid amin

- Cc phn ng ca nhm carboxyl
To mui vi base
2 R CH COOH
Cu 2
H
N
O C
O
H Cu H
R CH N
O
H
NH2
To ester
H2N
CH COOH
C2H5OH
HCl
CH COOH
C O
AgCl
Ag2O
H2N
CH COOC2H5
R
Tc dng vi PCl5
H2N
Mu xanh thm
R
+
NH3 CH COOC2H5 Cl-
R
H 2O
CH
NH3 CH COCl Cl-
PCl5
Phn ng loi nhm COOH (decarboxyl ha)

H2N
CH COOH
R
t0
H2N
CH2 R
CO2
65
POCl3
- Cc phn ng ca nhm amino

Phn ng vi acid nitr (HNO2)
H2N
CH COOH
HNO2
HO
HO N N CH COOH
CH COOH
N2
Hp cht diazoic
Phn ng alkyl ha (RX)

H2N
CH2
COOH
CH3I
HN
CH2 COOH
CH3I
(CH3)2N
CH2 COOH
CH3I
CH3
Phn ng alcyl ha (RCOCl)

CH3COCl
H2N CH2
COOH
CH3CONHCH2COOH
Phn ng to imin vi hp cht carbonyl

R'
H2N
CH COOH
R
R'
CH COOH
R
66
(CH3)3N
I-
HCl
CH2 COOH
Phn ng vi thuc th Ninhydrin

O
C O
Ninhydrin
H2N
CH COOH
_H O
2
C N CH COOH
R
t0
H2O
N CH R
O
H
C
O
NH2
NH2
O C
O
_ H+
O
C
N
O
O
Phc mu xanh tm
67
RCHO
- Cc phn ng do s tham gia ca hai nhm carboxyl v amino

-aminoacid
O
R CH C OH
H HN
NH H
HO C CH R
O
R CH
NH
C
O
_ 2 H2O
Dicetopiperazin
NH
CH R
-aminoacid
R CH CH2 COOH
NH2
_ NH3
R CH CH COOH
Cc , , -aminoacid
CH2
CH2
CH2
H2C
NH2 HO
CH2
H2C
CH2
HO
NH2
CH2
H2C
H2O
4-Butanlactam
NH
CH2
CH2
H2C
CH2
H2C
NH
H2 O
5-Pentanlactam
68
1.5.2 Peptid
1.5.2.1 nh ngha v danh php
Peptid l amid c hnh thnh do cc chc acid v chc amin ca

cc acid amin tng tc vi nhau. Ty vo s acid amin ngi ta
chia peptid thnh: dipeptid, tripeptid,polypeptid.
H2N
CH COOH
H2N
CH COOH
H2O
H2N
CH C
R
NH CH COOH
Lin kt peptid
Qui c gi tn peptid
CH3
H3C
H3C
CH
H 3N
CH
CH2 C NH CH C O
O
Glycylvalin
(Gly-Val)
CH3
H3N
CH C NH CH2 C O
O
Valylglycin
(Val-Gly)
69
H3C
CH3
O
CH
H3N
CH2 C NH
CH C NH CH C O
O
Glycylvalylphenylalanin
CH2
C- cui mch
N- cui mch
(Gly-Val-Phe)
O
NH2
C NH CH C NH CH2 C O
O
Pro-Leu-Gly
CH2
CH
CH3 CH3
H3N
Cu ni disulfur
CH2
CH2
CH C
O
NH CH C NH CH C NH CH C NH CH C NH CH C O
CH2 O
CH2 O
CH2 O
(CH2)3
CH2
COOH
OH
CyS-Tyr-Phe-Glu-CyS-Arg
70
NH2
1.5.2.2 Xc nh cu trc ca peptid

C nhng acid amin no trong phn t
C bao nhiu acid amin trong phn t
Nh my phn tch amino acid
Trt t lin kt gia cc acid amin trong phn t
* Thuy giai bang dung dch HCl 6M.

* Sac ky cot.
o hap thu
Serin Prolin
Glycin
Acid aspartic
Cystin
20
60
100
140
180
260
220
71
Dung dch giai ly
(ml)
Phng php gim cp Edman :
H 3C
Phenylisothiocyanat
C6H5NCS
CH3
O
CH
H3N
CH2 C NH
O
CH C NH CH C O
O
CH2
Glycylvalylphenylalanin
(Gly-Val-Phe)
- S gim cp s khng cn hiu qu sau 25 ln ct.

- i vi peptid v protein ln:
Thy gii bn phn cho ra mt s mnh nh
Tch ri cc mnh nh ny; xc nh th t acid amin ca tng mnh
nh bng s gim cp Edman
Sau cng tm hiu xem cc mnh ny ghp nhau nh th no
72
- May phan tch amino acid cho biet Angiotensin II

cha 8 amino acid khac nhau vi so lng bang
nhau la : Arg, Asp, His, Ile, Phe, Pro, Tyr, Val.
- Angiotensin II co au N la acid
Aspartic.
- Thuy giai ban phan bang dung dch HCl loang,
nh phng phap Edman a xac nh c cac
manh la : Arg-Val-Tyr; Ile-His-Pro; Asp-Arg-Val; ProPhe; Val-Tyr-Ile.
Asp-Arg-Val
Arg-Val-Tyr
Val-Tyr-Ile
Ile-His-Pro
Pro-Phe
73
Asp-Arg-Val-Tyr-Ile-His-Pro-Phe
1.5.2.3 Tng hp peptid

Bo v nhm chc amin
H3N
CH COO
C6H5CH2OCOCl
Q= C6H5CH2OCO
Q NH CH COOH
(Carbobenzyloxyclorid)
HCl
Q NH CH COCl
R
To lin kt peptid
Q NH CH COCl
H3N
CH COO
Q NH CH CONH CH COOH
R'
R'
Gii phng chc amin

Q NH CH CONH CH COOH
R
R'
H3N
CH CONH CH COO
R
R'
74
1.5.3 Protid
nh ngha v phn loi
Protid l nhng polypeptid c phn t lng ln (>10.000)
Phn loi:
Da vo hnh dng : protid hnh cu v protid hnh si
Da vo thnh phn cu to: holoprotein v
heteroprotein
Da vo chc nng ca protein: protein cu trc, vn chuyn,
xc tc, ti thng tin
Tnh cht
- Cht keo, khng c nhit nng chy c trng
- Quang hot, quay tri
- Protein b bin tnh di tc dng ca nhit, pH
75
Cu trc protid
- Cu trc bc mt
- Cu trc bc ba
Ch s lng, thnh phn,

th t ca cc acid amin
Ni n tt c cc on cu trc bc
hai, ton th phn t protein s cun
thnh hnh g trong khng gian ba chiu
- Cu trc bc hai
Mch polypeptid c dng xon c
hay gp khc l do lin kt hydro
gia cc chc C=O, NH2, COOH
v COO- ca hai amid khc nhau
- Cu trc bc 4
Khi ni n vic kt hp hai hoc
nhiu chui dy peptid trong mt
protein hon chnh.
76
Nguyn Th Thu Trm
1.6 Lipid
1.6.1 nh ngha
- L hp cht hu c c trong ng vt, thc vt
- Thng l ester ca acid bo (i khi l dn xut ca acid bo)
- Khng tan trong nc, tan trong dung mi hu c, khng bay
hi, nht cao
1.6.2 Phn loi
1.6.3 Vai tr v ng dng
Lipid n gin
- D tr nng lng, l yu t cu
- Triglycerid (cht bo) trc c bn ca c th sng
- Serid (sp)
- Trong cng nghip, lipid dng
sn xut x phng, sn, vecni
- Sterid
Lipid phc tp
- Phospholipid
- Glycolipid
- Trong ngnh dc, lipid dng lm

dung mi pha ch thuc tim, lm
t dc thuc m,77thuc cao dn.
1.6 Lipid
MT S ACID BO THNG GP
Tn
Cu to
S
cacbon
tnc
( 0C)
Acid no
Lauric
12
CH3(CH2)10COOH
44
Myristic
14
CH3(CH2)12COOH
58
Palmitic
16
CH3(CH2)14COOH
63
Stearic
18
CH3(CH2)16COOH
70
Arachidic
20
CH3(CH2)18COOH
75
Palmitoleic
16
CH3(CH2)5CH=CH(CH2)7COOH (cis)
32
Oleic
18
CH3(CH2)7CH=CH(CH2)7COOH (cis)
Ricinoleic
18
CH3(CH2)5CH(OH)CH2CH=CH(CH2)7COOH (cis)
Linoleic
18
CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH (cis)
-5
Linolenic
18
CH3CH2(CH=CHCH2 )2CH=CH(CH2)7COOH (cis, cis,

78
cis)
Acid cha
no
-11
1.6 Lipid
- Glycerid (cht bo): l ester ca acid bo cao, khng nhnh vi glycerin

CH2
C17H35COOH acid stearic

C15H31COOH acid palmitic + glycerin
C17H33COOH acid oleic
R1
O
CH
R2
O
CH2
R3
- Serid (sp): l ester ca acid v alcol bo cao

C15H31COOH + C30H61OH
Acid palmitic
Alcol miricylic
C15H31COOC30H61 + H2O
Sp ong
- Sterid: l ester ca acid bo cao vi alcol vng nh sterol
Cholesterol
Sterid
79
1.6 Lipid
- Phospholipid:
O
CH2 O C
R2
O
CH2 O C
R1
R2
C O CH
P O CH2 CH2 NH3
CH2 O
R1
C O CH
P O CH2 CH2 N(CH3)3
CH2 O
Phosphatidyletanolamin (Cephalin)
Phosphalidylcholin (Lecithin)
- Glycolipid: gm 2 nhm chnh l ceramid v cerebrosid

CH2 OH O OH
CH NH C
CH3
(CH2)4
CH CH (CH2)3
CH CH2
Loi ceramid
R = C17H35 n C23H47
CH OH
OH
HO
HO
CH3 (CH2)5
O
OH
CH CH (CH2)3
O CH2
O OH
CH NH C
CH CH OH
OH
CH
Loi cerebrosid
R = C14 n C22 (mch thng)
80
1.6 Lipid
- Phn ng thy phn

O
CH2 O C R
O
CH O
C
O
R'
CH2 O C
R''
H2O
CH2 OH
CH OH
RCOOH
R'COOH
R''COOH
CH2 OH
O
CH2 O C R
O
CH O
C
O
R'
CH2 O C
R''
HCl
CH2 OH
CH OH
RCOOH
R'COOH
R''COOH
CH2 Cl
3-Monocloropropan-1,2-diol
(3-MCPD)
- Phn ng cng (H2/Ni, X2)

81
1.6 Lipid
Hin tng cht bo b i

H H
(CH2)n
H H
O2
(CH2)n
(CH2)n
(CH2)n
O O
(CH2)n
OH
H C
(CH)2n
Cc ch s ha hc ca cht bo
- Ch s acid: l s mg KOH cn thit trung ha cc acid t do c trong
1g cht bo.
- Ch s x phng ha: l s mg KOH cn thit trung ha cc acid t do
v x phng ha cc ester c trong 1g cht bo.
- Ch s ester: l s mg KOH cn thit x phng ha cc ester c trong
1g cht bo.
- Ch s iod : l s gam iod kt hp vi 100g cht bo.
82
1.6 Lipid
X phng: l hn hp mui kim ca cc acid bo

H2O
NaOOC
COONa
H2O
H2O
DU
COONa
H2O
NaOOC
H2O
Cht ty ra tng hp
O
O
O
S
O
ONa
Natri alkyl benzensulfonat
83
Natri luarylsulfat
ONa
O
2 Hp cht d vng
2.1 nh ngha:
Hp cht d vng l hp cht hu c c cu to vng, trong vng
cha mt hoc nhiu nguyn t ca cc nguyn t khc ngoi
carbon (N, O, S...)
2.2 Phn loi:
Theo d t: hp cht d vng cha N, O, S
Theo vng: d vng 3, 4, 5, 6, 7cnh
Theo mc cha no ca vng: d vng thm, d vng khng
thm
2.3 Danh php:
N
Tn thng thng
Pyrol
N
Piridin
Nguyn Th Thu Trm
Furan
Quinolin
Thiophen
Isoquinolin
84
D t
Oxy
Tip u ng
Tn IUPAC: da vo 4 yu t: tip 2 Hp cht d vng

u ng, vng, mc cha no
ca vng, v tr ca d t
Oxa
Lu hunh Thia
Selen
Selena
Nit
Aza
Phospho
Phospha
H
N
H
O
Azirin
Aziridin
Oxazol
Thiepan
Tip v ng thng dng

S cnh
ca vng
T c
bn
Vng c Nit
Vng khng c Nit
C s lin
kt i ti a
Bo ha
C s lin kt
i ti a
Bo
ha
-ir-
irin
iridin
iren
iran
-et-
et
etidin
et
etan
-ol-
ol
olidin
ol
olan
-in-
in
in
an
-ep-
epin
epin
epan
-oc-
ocin
ocin
Nguyn Th Thu Trm
85
ocan
1,2-Dioxolan
2 Hp cht d vng
Hp cht d vng 5 cnh

N
Pyrol
Thiophen
Furan
Tnh thm ca Thiophen Pyrol Furan

Nhm furan
Br2
Phn ng th:
Br
NO2
Br
Br
HNO3
SO3/pyridin
O
SO3H
COCH3
(CH3CO)2O
AlCl3
RLi
Nguyn Th Thu Trm
Li
CO2
86
O
COOLi
2 Hp cht d vng
Phn ng cng
H2/Ni
O
O
O
Phn ng Diels-Alder
O
Nhn furan km bn, c th b ph v bi phn ng hydrogen ha hay oxy ha

hay Pb(CH3COO)2 /CH3COOH
H2/Pt
CH3COOH
CH3CH2CH2CH2OH
O2
O
V2O5
Pb(CH3COO)2
CH3COOH
Nguyn Th Thu Trm
HOCCH=CHCHO
87
2 Hp cht d vng
Nhm pyrol
T c
Nhm thiophen
Hp cht d vng 6 cnh

Nhm pyridin
Phn ng th thn in t
Pyridin
Quinolin
Benzoquinolin
Phn ng th thn hch
88
Nguyn Th Thu Trm
2 Hp cht d vng
Phn ng th thn in t
NO2
KNO3, H2SO4
300
N
SO3H
H2SO4
350
N
N
Br
Br2
300
Br
N
RX / RCOX (AlCl3)
Br
Khng xy ra phn ng
Friedel-Craft
Phn ng th thn hch

NaNH2
N
N
NH2
C4H9Li
N
C4H9
89
Nguyn Th Thu Trm
2 Hp cht d vng
Phn ng oxi ha
Vng pyridin khng b oxi ha bi dd brom, KMnO4 long. Gc hydrocarbon gn
trn khung pyridin d b oxi ha to acid.
[O]
N
CH3
COOH
Phn ng kh
H2/Pt
hoc Na + C2H5OH
N
H
Tnh base
90
Nguyn Th Thu Trm
2 Hp cht d vng
Mt s hp cht d vng ng dng lm thuc

Nguyn Th Thu Trm
91
2 Hp cht d vng
Alcaloid l dn xut ca pyridin v piperidin

Ricinin C8H8O2N2
OMe
CN
Pyridin
Piperidin
Me
NO2
NO2
Me
COOH
K2Cr2O7
H2SO4
N
O
CONH2
NH3
- 33 0C
N
O
OMe
COOH
PCl5
POCl3
COOMe
MeOH
HCl
MeONa
OMe
OMe
Cl
OMe
CN
CN
MeONa
Cl
OMe
CN
MeI
,P
OMe
N
Me
2 Hp cht d vng
Nicotin
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.
2 Hp cht d vng
CH3
N
Picolin
(2, 3 hoc 4-)
COOH
N
[O]
KMnO4
COOH
N
Acid pyridin carboxylic
(2, 3 hoc 4-)
Acid nicotinic (Niacin, acid 3-pyridin

carboxylic) cha bnh bch tng. Amid ca
n l vitamin PP.
CONHNH2
Isoniazid, Rimifon, cha bnh lao

N
2 Hp cht d vng
Piperin (alcaloid ca ht tiu en)
O C
CHCl3
NaOH
R.T
HO
Catechol
O
HO
CHO
O
O
CH2I2
NaOH
HO
CH CH CHO
Ac2O
NaOH
PCl5
CH CH CH CH
HO
CH3CHO
Piperin
AcONa
CH CH CH CH COCl
CHO
O
O
CH CH CH CH COOH
O
O
O C
O
HN
CH CH CH CH
C6H6
Piperin
2 Hp cht d vng
Bot tieu en (10g)

- Trch nong vi ru etylic
95%, 2h
- Loc
Ba
Dch alcol
- Co quay thu hoi

moi
-dung
Them
dung dch KOH/alcol 10% (10
ml)
- e lang (loai phan
khong tan)
Piperin
2 Hp cht d vng
Khong 25 loi,
chia thnh 2 nhm
ty theo c cu.
Cy phin (anh tc) Papaver somniferum L.

@ Alcaloid thuc nhm isoquinolin
MeO
MeO
MeO
MeO
N
MeO
Me
MeO
Me
OMe
OMe
OH
OMe
OMe
OMe
Papaverin
Laudanosin
Laudanin
2 Hp cht d vng
@ Alcaloid thuc nhm phenantren
HO
MeO
2
3
13
14
5
8
6
7
Morphin C17H19O3N
14
HO
N CH3
6
7
Codein C18H21O3N
10
12
13
14
5
15
16
15
16
15
HO
N CH3
13
1
11
10
12
2
3
11
10
12
11
MeO
2
3
MeO
N CH3
16
8
6
7
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.
2 Hp cht d vng
HO
HO
2
3
1
11
10
12
13
14
5
16
15
HO
6
7
O
N CH3
9
13
HO
14
N CH3
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)?
2 Hp cht d vng
HO
CH3
2
3
O
10
12
13
14
N CH3
10
12
CH3COOH
bng
1
11
13
14
5
16
15
16
15
8
2
3
11
HO
C O
CH3
C O
6
7
Heroin
Morphin
Methadone
O
N
N CH3
3 Hp cht thin nhin
3.1 Acid nucleic

Acid nucleic l mt polyester ca acid phosphoric +
ng pentose + base hu c.
Base
ng
O
O P O
Base
ng
O
O P O
Nucleosid
O
Nucleotid
Phn ng : D(-) ribose v D(-)-2-deoxyribose.

Phn base : purin v pyrimidin.
3 Hp cht thin nhin
Phn ng ca acid nucleic

1
CHO
Acid Ribo Nucleic

(ARN)
HOH2C
OH
OH
OH
CH2OH
D(-) Ribose
OH
O
H
H
OH
OH
-D(-) - Ribofuranose
CHO
Acid Deoxyribo Nucleic H
OH
OH
(ADN)
HOH2C
4
OH
O
H
3
OH
H
2
CH2OH
D (-)-2-Deoxyribose
-D(-) 2-Deoxyribofuranose
3 Hp cht thin nhin
Phn base ca acid nucleic

6
1
Cc base purin
N
3
NH2
NH2
6
1
N
3
NH2
CH3
N
5
1-Metiladenin
N
H
Purin
N
5
6
1
H2N
O
H
6metilaminoadenin
CH3HN
N
3
H2N
O
H
N
3
O
CH3
H2N
N
5
6
1
(CH3)2N
6
1
Guanin
Adenin
CH3NH
N
2
2-Metilaminoguanin 2-Dimetilaminoguanin
1-Metilguanin
Cc base pyrimidin
3 Hp cht thin nhin
N
N
NH2
O
H
Uracil
CH3
N
N
H
Cytosin
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-2-deoxyribose,
acid photphoric, adenin, guanin, cytosin, thymin
3 Hp cht thin nhin
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 :
NH2
6
5
N7
N9
N
3
HOH2C
O
H
OH
H
OH
Adenosin (Ribose + Adenin)
H2N
HOH2C
H
H
N
N
O
H
OH
H
OH
Guanosin (Ribose + Guanin)
3 Hp cht thin nhin
Lin kt glycosid
NH2
O
H
H
H
H
OH
Thymidin (Deoxyribose + Thymin)
N
3
O
HOH2C
O
HOH2C
CH3
HOH2C
OH
H
OH
Cytidin (Ribose + Cytosin)
O
H
OH
H
OH
Uridin (Ribose + Uracil)
3 Hp cht thin nhin
Cu to ca nucleotid
Nucleotid l nucleosid photphat
O
NH2
6
O
O
N
O
HOH2C
O
H
N7
N9
N
HOH2C
H
H
OH
P OH
OH
Adenosin phosphat
H
H
O
O
H
H
OH
P OH
OH
Uridin phosphat
3 Hp cht thin nhin
CU TO CA ACID NUCLEIC
3 Hp cht thin nhin
8
9
6
1
4
3
3 Hp cht thin nhin
3.2 Terpenoid
Terpen l nhng hydrocarbon c cng thc
chung l bi s ca phn t isopren (C5H8)n
n CH2 C CH CH2
CH2 C CH CH2
CH3
CH3
Isopren
ui
ui
Monoterpen
3 Hp cht thin nhin

3
2
4
5
CH2OH
1
6
7
8
14
1
2
3
10
4
15
CH2OH
8
7
11
13
12
3 Hp cht thin nhin
(C5H8)n
n=1
C5H8
Hemiterpen (isopren)
n=2
C10H16
Monoterpen
n=3
C15H24
Sesquiterpen
n=4
C20H32
Diterpen
n=5
C25H40
Sesterterpen
n=6
C30H48
Triterpen
n=n
(C5H8)n
Polyterpen (cao su thin nhin)
3 Hp cht 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
3 Hp cht thin nhin
- Tinh du cy Myrcia acris.
3
2
4
5
- Cht lng, ts = 166-168oC
1
6
- Ozon gii (CH3)2C=O,
HOC(CH2)2COCHO, HCHO
Myrcen
(7-Metil-3-metilenocta-1,6-dien)
Myrcia acris
3
4
5
6
- Tinh du l hng qu (Ocimum

basilicum).
- Cht lng, ts = 81oC/30mmHg
- Ozon gii CH3COCHO, HCHO

Ocimen
HOCCH2CH2COCH3
8
(3,7-Dimetilocta-1,3,7-trien)
Ocimum basilicum
3 Hp cht thin nhin
Cc dn xut ca monoterpen khng vng

Dn xut alcol
1
CH2OH
3
4
trans
cis
Geranio
l
OH
Nerol
CH2OH
Linalol
CH2OH
1
Citronellol
3 Hp cht thin nhin
(5 tan)
1 kg tinh
dau
30-40%
Geraniol1
CH2OH
5-10%
Nerol
3
4
5
35-55%
Citronellol
CH2OH
1
Cac
thanh
3
2
4
5
6
CH2OH
1
phan
khac
3 Hp cht thin nhin
Dn xut aldehyd
1
CHO
3
4
Geranial, Citral a
CHO
5
6
7
8
Neral, Citral b
CHO
1
Citronellal
iu ch Citral b trong cng nghip:

BrH2C
C2H2
C
CH3
CH3
C2H5OOC
HC
NaNH2
OH
C
H3C
H2/Pd
H2C=HC
H3C
CH3
OH
PBr3
OH
O H O, HO2
ClCH2COOC2H5
Zn
-H
COOC2H5
C
H3C
CH3
2O
C2H5OOC
CH3
HBr
1.DIBAH
+
2. H3O
COOC2H5
CHO
Citral b
3 Hp cht thin nhin
CH3
CHO
(CH3)2CO
H2O
CH3
CH3
Citral a
H
CH3
C
CH3
C
O
H
-Ionon
Vitamin
A
-Ionon
3 Hp cht thin nhin
CN
BrCH2CN
OH
Zn
COOH
H2O
ROH (H+)
2. LiAlH4
3. MnO2
1.
CH3
COOR
(C6H5)3P
CH C
CH COOR
CHO
LiAlH4
CH2OH
Vitamin A :
Vitamin A
- Chat ket tinh mau vang,

t0nc = 640C.
- Giup sang mat.
- Lan au tien c tm
thay trong dau gan ca
(1931).
3 Hp cht thin nhin

7
6
5
Khung p-mentan
4
8
10
Limonen
-Terpinen
1,8-Mentadien (
1,8
-Terpinen
-Mentadien)
-Terpinen
Terpinolen
-Phelandren -Phelandren
3 Hp cht thin nhin
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
OH
-Terpineol
T -Pinen (thnh phn chnh trong tinh du

thng) iu ch -Terpineol, cis-Terpin-1,8, Cineol1,8.
3 Hp cht thin nhin
OH
CH(CH3)2
CH(CH3)2
OH
CH3
CH3
CH(CH3)2
OH
CH(CH3)2
CH3
OH
OH
CH3
3 Hp cht thin nhin

OH
O
OH
OH
-Pinen
-Terpinol
OH
cis-Terpin-1,8
H2 O
H 2O
H 2O
H+
H+
cis-Terpin-1,8 Cineol-1,8
trans-Terpin-1,8
OH
OH
OH
H
H+
H2O
H2O
H
O
OH
Cineol-1,8
CH3
3 Hp cht thin nhin
2
1
3
6
4
7
5
Pinan
Thuyan
Caran
Camphan
(Bornan)
Fenchan
2
5
2
4
2,6,6-trimetilbicyclo[3.1.1]heptan
1,7,7-trimetilbicyclo[2.2.1]heptan
3 Hp cht thin nhin
Nhm pinan
10
1
0
2
1
8
6
9 4
3
9
-Pinen
-Pinen
Nhm Camphan
10
6
8
9
7
10
Camphor
2
4
3 Hp cht thin nhin
Tng hp Camphor t -Pinen

-Pinen
Cl
HCl
15o
CH2
Cl
Cl
HCl
CH2
H3C C O
CH3COOH
Camphen
Cl-
H2O
HO
O
O
CH3COOH
Campho
r
3 Hp cht thin nhin
Sesquiterpen C15H24
Sesquiterpen khng vng (c 4 lin kt i)
Sesquiterpen 1 vng (c 3 lin kt i)
OH
OH
HOH2C
-Facnesen
(trong tinh du s)
-Salinen
(trong tinh du cn ty)
Punctaporonin A
3 Hp cht thin nhin
Diterpen C20H32
Diterpen khng vng & Diterpen vng
Diterpen khng vng
1
11
16
CH2OH
3
2
Phytol
(2E-7R,11R)-3,7,11,15-Tetrametilhexadeca-2-enol
O
CH3
gc Phytyl
Vitamin K1 (2-metil-3-phytyl-1,4-naphtoquinon)
3 Hp cht thin nhin
Diterpen vng
1
2
10
11
B
12
13
14
8
1-metil-7-isopropilphenanthren
CH3
COOH
CH3
Acid Abietic
CH3
COOH
CH3
Acid Sapietic
3 Hp cht thin nhin
POLYTERPEN (C5H8)n
- Cao su thin nhin
CH3
CH2 C CH CH2 n
CH2
Polyisopren
CH2
CH2 CH2
C C
C C
H
CH3
H CH3
CH2 CH2
C
C
H
CH3
Nha cao su - dng cis
CH3
CH2
C C
CH2
H
CH2
C
CH3
CH3
C
CH2
CH2
C C
H
CH2
Nha Kt (gutta-percha) - dng trans
3 Hp cht thin nhin
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
3 Hp cht thin nhin
- 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
3 Hp cht thin nhin
3.3 Steroid
Khung gonan
(1,2-cyclopentanoperhydrophenanthren)
Sterol
Acid mt
Ni tit gii tnh
Ni tit thng thn
(Cortinoid)
Glycosid tim
Sapogenin
Steroid alcaloid
3 Hp cht thin nhin
- Cch nh s
21
12
11
1
2
10
16
19
1
15
5
4
14
23
18
HO
17
11
13
24
16
9
8
10
14
15
7
5
4
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
26
12
17
13
22
20
dy (allo)
dy (normal)
25
27
13
D
C
B
3 Hp cht thin nhin
A&B: trans
dy (allo)
13
C
B
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 ).
3 Hp cht thin nhin
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
3 Hp cht thin nhin
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).
- 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.
HO
Cholesterol
- Khi lng LDL > HDL th t l

cholesterol trong mu s tng ln gy
triu chng bnh tim mch nguy him.
H2/Pt
HO
Cholesterol
Zn/Hg, HCl
CrO3
HO
Cholestanol
Cholestanon
Cholestan
3 Hp cht thin nhin
Ergosterol (C28H44O)
- Tinh th, tnc= 163oC, []D= -130

- Ergosterol v cholesterol l
nguyn liu sn xut vitamin D2
v D3
R
HO
Ergosterol
R
OH
Tin vitamin D
h
Ergosterol
HO
h
R
R
CH2
HO
HO
Tachysterol
HO
Lumisterol
Vitamin D2
(Ergocalciferol)
3 Hp cht thin nhin

R
OH
Tin vitamin D
h
h
HO
7-Dehydrocholesterol
R
R
CH2
HO
HO
Vitamin D4 : R =
HO
Vitamin D3 (Cholecalciferol)
3 Hp cht thin nhin
Stigmasterol (C29H48O)
29
28
22
21
18
19
20
23
17
11
13
24
25
27
- Tinh th, tnc= 1700C, []D= -40
26
- Trong du u nnh, tn ti
di dng acetat
1
9
3
HO
15
7
Stigmasterol
29
28
21
18
19
22
20
23
17
11
13
1
9
Sitosterol
HO
15
7
24
25
26
27
3 Hp cht thin nhin
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
COOH
27
24
C24
C27
Cholesterol
CrO3
H2/Pt
HO
HO
Zn Hg/ HCl
Cholestanol
Cholestanon
COOH
CrO3
H
Cholestan
Acid allo Cholanic (5Cholanic)
Cholesterol
H2/Pt
Oxy ha Oppenauer
O
HO
1.
2.
CrO3
HO
Cholet-4-en-3-on
Coprostanon
COOH
CrO3
Zn Hg/ HCl
H
Coprostan
Acid Cholanic (5 -Cholanic)
3 Hp cht thin nhin
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
19
Khung Estran
Estrogen
Khung Androstan
Androgen
Khung Pregnan
Progestagen
20
3 Hp cht thin nhin
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
OH
OH
OH
HO
HO
HO
Estron
Estriol
17 -Estradiol
HO
17-Estradiol
3 Hp cht thin nhin
- Progestagen
Khung Pregnan
OH
HO
Progesteron
Pregnandiol
3 Hp cht thin nhin
- Hormon sinh dc nam:
Khung Androstan
O
O
HO
HO
Androstero
n
5-iso-androsteron
OH
HO
Dehydro epi androsteron
Testosterol
Cc hormon tuyn thng thn
3 Hp cht thin nhin
OH
21
O
X
HO
X = OH : Glucocorticoid
17
11
X = H : Mineralocorticoid
1
3
O
OH
CHO
HO
Aldosteron
Cc mineralocorticoid c tc
dng tng thi K+, H+, ti hp thu
Na+ v gi nc.
3 Hp cht thin nhin
Cc Glucocorticoid tc ng ln s chuyn ha glucid, protid, lipid.

OH
OH
O
O
HO
Cortison
Corticosteron
OH
O
HO
Cortisol
OH
OH
3 Hp cht thin nhin
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.
Truc ao, Nerium

Dng a hoang hoa tm,
oleaner L. Ho Truc
Digitalis purpurea L. Ho Hoa mom
ao Apocynaceae
soi Scrophulariaceae.
Bong bong, Calotropis gigantea (L.)
Dryand ex.Ait. Ho Thien ly
3 Hp cht thin nhin
Cau truc cua glycosid tim

@ Cau truc phan ng:
CH2OH
H
O
H
OH
OH
OH
O
CH3
OH
O
CH3
OH
OH
H
H
OH
OH
-D-Glucopyranose
OH
OH
-L-Rammose
OCH3
-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
Cau truc
aglycon:
trong phan
o co
glucose th glucose se
ng
v
tr cuoi
cung.
Tat ca
cac
aglycon
eu co nhan 4 vong
chung cho cac hp chat steroid. Cac vong A

& B: trans hay cis
3 Hp cht thin nhin
@ Cau truc phan

aglycon:
11
1
ng
1
4
OH
1
2
5
4
1
6
- 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.
3 Hp cht thin nhin
Lin quan gia cu trc v hot tnh sinh hc

O
CH3
CH3
H3C
H3C
H3C
HO
HO
O
HO
OH
O
O
O
O
OH
Digitoxi
n
- A & B: cis ; B & C: trans ; C

& D: cis
Good
luck to
you
1) Mt monoterpen (X) c CTPT C10H16 c tch t tinh du cy

nguyt qu. (X) cng 3 mol H2 th thu c mt hidrocacbon
C10H22 (Y). Ozon ha (X) ri thy phn cho cc sn phm sau:
CH3COCH3, HCHO, HOC-CH2-CH2-CO-CHO.
Da vo quy tc isopren hy cho bit cng thc cu to ng
ca (X), (Y).
2)
Mt terpen (X) c CTPT C10H16 c tm thy nhiu

trong v cam, v chanh. (X) hp th 2 mol H2 thu c pmentan, C10H20. Ozon ha (X) ri thy phn thu c cc sn
phm sau:
CH3 C CHv
2 CHHCHO
2 CH CH2 CHO
O
C
O
CH3
a/ Trong phn t (X) c bao nhiu vng?

b/ Da vo quy tc isopren hy cho bit cng thc cu to
ng ca (X)
3) Ngi ta thit lp cng thc cu to ca -terpinol

bng dy chuyn ha sau:
Acid p-toluic + H2SO4 bc khi A (C8H8O5S)
A + KOH, un nng chy B (C8H8O3)
B + Na, ru C (C8H14O3)
C + HBr D (C8H13O2Br)
D + base, un nng E (C8H12O2)
E + C2H5OH, HCl F (C10H16O2)
F + CH3MgI, ri H2O -terpinol (C10H18O)
Cho bit cu to ca cc cht t A n F v ca terpinol.
4) Ngi ta thit lp cng thc cu to ca mentol bng

dy chuyn ha sau:
Etyl -metylpimelat + etoxid natri, ri H2O X
(C10H16O3)
X + etoxid natri, sau isopropyl iodua Y (C13H22O3)
Y + OH-, un nng, sau H+, un nng (C10H18O)
Bit CTCT ca etyl -metylpimelat :
C2H5OOCCH2CH2CH2CHCH2COOC2H5
CH3
1. (1S, 2R)-Ciclohexandiol ng vi cu trng no sau y

H
OH
OH
H
1
OH
2
OH
OH
OH
2. Thc hin chui phn ng sau

Cl
HNO3
NaOH
300 0 C
Fe / H+
Ac2O
D (Paracetamol)
In vivo trong ting Latin c ngha l qu trnh din ra trong c th

sng. Phng php in vivo c dng ch nhng th nghim
dng cc m sng hay ton b c th cn sng lm i tng th
nghim. Cc phng php in vivo khc vi in vitro (th nghim
ngoi c th sng, th nghim trong ng nghim) v cc th
nghim trn cc m hay c th cht. Thng thng, khi ni n
in vivo, ngi ta thng ngh n cc th nghim, th nghim trn
i tng l sinh vt sng. Cc th nghim s dng ng vt hay
cc th nghim lm sng trn ngi l v d ca nghin cu in
vivo.
Christopher Lipinksi v Andrew Hopkins 1 cho rng d th nghim
trn c th sng tm kim cc loi dc phm mi hay c thm
hiu bit v c th sinh vt vn phi ng thi xem xt nhng
cng c ha hc v bn cht ha hc ca i tng sinh vt. Thc
t cho thy mt hp cht no biu hin hot tnh khi c th
nghim ngoi c th sng (in vitro) nh kh nng kt hp vi
protein ti t hp, thay i qu trnh trao i cht t bo hay thm
ch ph v cu trc t bo c phn lp v.v. nhng cha chc
c hot tnh mong mun khi th nghim trn c th sng.
Chnh v vy th nghim in vivo vn c coi l bc th nghim
chc chn nht sau khi cc phng php in vitro c tin
hnh.
Mt quan
st vin
(1)
(2)
(3)
(4)
(5)
(6)
(1) Ngun sng
(4) nh sng phn cc
(2) nh sng thng
(5) ng cha mu
(3) Knh phn cc
(6) Knh phn gii
S trin quang k
159
SN2 mechanism
SN1 mechanism
160
Prostaglandin F2 l acid bo cha 20 carbon, gy au, sng,

Acid ny c bao nhiu ng phn lp th?
Xc inh cu hnh lp th ca cu trc di y.
161
- iu tr au ty, ban nt do ci
- Cha m nghn cho ph n mang thai
B s sinh b d tt tay, chn do m dng

Thalidomide trong qu trnh mang thai
162
Lactose
OH
OH
CH2OH
H
HO
H
H
CH2OH
O
OH
HO
H
OH
OH
H
CH2OH
H
HO
H
H
CH2OH
O
OH
HO
H
OH
OH
4-O-(-D-Galactopyranosyl)-D-glucopyranosid
Lactose hin din nhiu trong sa ngi, sa b (50g/lt).

Trong mng rut c enzym lactase sn sng thy gii
lactose thnh glucose v galactose.
163
OH
OH
O
O
HO
OH
6-(O--D-Galactopyranosyl)-D-galactopyranosid
OH
O
HO
OH
OH
CH2OH OH
HO
CH2OH
O
HO
OH
HO
CH2OH
164
4-(O--D-Mannopyranosyl)--D-fructofuranosid
OH
OH
O
.
HO
OH
-D-Galactopyranosyl (16)--D-glucopyranosyl
(1 2)--D-fructofuranosid
O
O
HO
HO
O
OH
CH2OH
O
HO
OH
CH2OH
OH
HO
HO
OH
O
O
HO
HO
-D-Glucopyranosyl (16)--Dglucopyranosyl (1 2)--Dfructofuranosid
CH2OH
O
OH
O
HO
CH2OH
165
OH
Cau 2: Goi ten cac ng theo

danhOH phap
IUPAC
OH
OH
O
O
HO
OH
-D-Galactopyranosyl (14)--Dglucopyranosyl (1 6)--Dglucopyranosid
HO
OH
O
HO
OH
HO
OH
OH
O
HO
HO
OH
OH
-D-Galactopyranosyl (12)--Dglucopyranosyl (1 2)--Dfructofuranosid
O
HO
CH2OH
O
HO
OH
CH2OH
OH
166
Gentiobiose
Trehalose
1-(O--D-Glucopyranosyl)--D-glucopyranosid
Melibiose
167
OH
CH2OH
HO
H
H
H C
O
H
NaOH, H2O
OH
OH
HO
H
H
OH
NaOH, H2O
OH
OH
CH2OH
1.4 C
H
HO
OH
H
H
H
OH
arbohydrat
OH
CH2OH
CH2OH
D-Fructose
Resorcinol
CH2OH
HO
H
H
O
H
OH
OH
OH
HO
(nhanh)
OH
HCl
- 3 H2O
OH
HOCH2
HOCH2
CH2OH
CHO
Phn ng Selivanop
CHO
HCl
H C OH
HO C
4-Hidroximetylenfurfural
CH2OH
D-Fructose
OH
(chm)
H C OH
H C OH
CH2OH
D-Glucose
168
Sn phm
c mu
anh o

Baigiang

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Ni dung chnh

3 Hp cht thin nhin

3.1 Acid nucleic

Ti liu tham kho

1.1 Hp cht tp chc- Halogenoacid

1.1.1 Danh php

1.1 Hp cht tp chc- Halogenoacid

VD1: Gi tn cc hp cht sau theo danh php quc t:

VD2: Vit cu trc ha hc ca cc hp cht sau:

1.1 Hp cht tp chc- Halogenoacid

1.1.2 Phng php iu ch

(sn phm chnh)

(sn phm chnh)

CH3 CH2 COOH

CH2 CH2 COOH

Cng HX vo acid cha no

CH2 CH2 COOH

1.1 Hp cht tp chc- Halogenoacid

1.1.3 Tnh cht ha hc

(C CHE PHAN NG)

CH2 CH2 COOH

1.1 Hp cht tp chc- Halogenoacid

1.1 Hp cht tp chc- Halogenoacid

Monocloroacetic MCA (ClCH2COOH)

Dng tng hp acid malonic, ester malonat, cht mu...

EtOOC CH2 COOEt

1.1 Hp cht tp chc- Halogenoacid

Dicloroacetic DCA (Cl2CHCOOH)

Tricloroacetic TCA (Cl3CCOOH)

- Precipitation of macromolecules: proteins, DNA, and RNA.

1.1 Hp cht tp chc- Halogenoacid

1. Hy sp xp cc cht sau theo th t tnh acid tng dn

1.2 Hp cht tp chc- Hydroxyacid

1.2.1 Danh php

CH3 CH CH2 CH COOH

1.2 Hp cht tp chc- Hydroxyacid

1.2.2 Phng php iu ch

T aldehyd-ceton (iu ch -hidroxycarboxilic)

C6H5 C CH2 CH3

1.2 Hp cht tp chc- Hydroxyacid

Phn ng Reformatski (iu ch -hidroxycarboxilic)

T cc hp cht etylen oxid (iu ch -hidroxycarboxilic)

1.2 Hp cht tp chc- Hydroxyacid

1.2 Hp cht tp chc- Hydroxyacid

1.2.3 Tnh cht ha hc

1.2 Hp cht tp chc- Hydroxyacid

Co quay thu hoi dung moi

Cao hexan (cha Artemisinin tren 80%)

t tan trong nc, etanol;

Ket tinh sau 24-48h

- Tay mau bang than hoa

Artemisinin tinh khiet

1.2 Hp cht tp chc- Hydroxyacid

Humans, guinea pigs, some

1.2 Hp cht tp chc- Hydroxyacid

Cc phn ng khc ca alcolacid

Aspirin (acid acetylsalicilic)

1.2 Hp cht tp chc- Hydroxyacid

1.2.4 ng dng mt s alcolacid ph bin

- Chit xut t cy ma, c ci ng.

1.2 Hp cht tp chc- Hydroxyacid

Acid Lactic CH3CHOHCOOH

1.3 Hp cht hai chc c nhm carbonyl