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19700-21-1

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Basic Information
CAS No.: 19700-21-1
Name: GEOSMIN
Article Data: 13
Molecular Structure:
Molecular Structure of 19700-21-1 (GEOSMIN)
Formula: C12H22 O
Molecular Weight: 182.306
Synonyms: 4a(2H)-Naphthalenol,octahydro-4,8a-dimethyl-, [4S-(4a,4aa,8ab)]-; 4aa(2H)-Naphthol, octahydro-4a,8ab-dimethyl- (8CI); (-)-Geosmin;Geosmin
EINECS: 243-239-8
Density: 0.985 g/cm3
Boiling Point: 252.4 °C at 760 mmHg
Flash Point: 104.2 °C
PSA: 20.23000
LogP: 3.11780
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Synthetic route

Methanesulfonic acid (1aR,2S,4aS,8S,8aS)-4a,8-dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-2-yl ester

19700-21-1

(-)-geosmin

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Heating;90%
169869-40-3

(+)-(4S,4aS,5R,8aS)-trans-4,8a-dimethyl-4a,5-epoxydecalin

19700-21-1

(-)-geosmin

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 60℃; for 1h;64%
60563-48-6

C14H24OS2

19700-21-1

(-)-geosmin

Conditions
ConditionsYield
With nickel In ethanol
/PBBEC010-1980/

/PBBEC010-1980/

19700-21-1

(-)-geosmin

Conditions
ConditionsYield
Multistep reaction;
372-97-4, 13058-04-3, 25744-33-6, 27248-37-9, 27248-38-0, 40716-68-5

farnesyl pyrophosphate

A

(1S,4aS)-1,4a-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

B

19700-21-1

(-)-geosmin

C

23986-74-5

germacrene D

D

(–)-(4S,7R)-germacra-(1(10)E,5E)-dien-11-ol

Conditions
ConditionsYield
With Streptomyces coelicolor germacradienol synthase; Tris-Cl; magnesium chloride In water at 30℃; for 4h; Enzymatic reaction;
...Expand
2816-57-1

2,6-dimethylcyclohexanone

19700-21-1

(-)-geosmin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 33 percent / H2SO4 / toluene
2: 83 percent / KOH / methanol / 1.5 h / Heating
3: 81 percent / LiAlH4 / diethyl ether / 3 h
4: 89 percent / pyridine / 24 h
5: Li, EtNH2 / 2 h / -5 °C
6: 73 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C
7: 64 percent / LiAlH4 / tetrahydrofuran / 1 h / 60 °C
View Scheme
125515-66-4

(+)-4,8a-dimethyl-1,2,3,4,6,7,8,8a-octalin

19700-21-1

(-)-geosmin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C
2: 64 percent / LiAlH4 / tetrahydrofuran / 1 h / 60 °C
View Scheme
17990-00-0

(4aα,8β)-4a,8-Dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalinon

19700-21-1

(-)-geosmin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 81 percent / LiAlH4 / diethyl ether / 3 h
2: 89 percent / pyridine / 24 h
3: Li, EtNH2 / 2 h / -5 °C
4: 73 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C
5: 64 percent / LiAlH4 / tetrahydrofuran / 1 h / 60 °C
View Scheme
52252-49-0, 97345-21-6, 97345-22-7

6-hydroxy-4,8a-dimethyl-1,2,3,4,6,7,8,8a-octalin

19700-21-1

(-)-geosmin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 89 percent / pyridine / 24 h
2: Li, EtNH2 / 2 h / -5 °C
3: 73 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C
4: 64 percent / LiAlH4 / tetrahydrofuran / 1 h / 60 °C
View Scheme

(E)-2,6-dimethyl-2-(3'-oxobutyl)cyclohexanone

19700-21-1

(-)-geosmin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 83 percent / KOH / methanol / 1.5 h / Heating
2: 81 percent / LiAlH4 / diethyl ether / 3 h
3: 89 percent / pyridine / 24 h
4: Li, EtNH2 / 2 h / -5 °C
5: 73 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C
6: 64 percent / LiAlH4 / tetrahydrofuran / 1 h / 60 °C
View Scheme
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