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13190-97-1
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Basic Information
CAS No.: 13190-97-1
Name: Solanesol
Molecular Structure:
Molecular Structure of 13190-97-1 (Solanesol)
Formula: C45H74O
Molecular Weight: 631.082
Synonyms: Nicotine (Solanesol);Nonaisoprenol;2,6,10,14,18,22,26,30,34-Hexatriacontanonaen-1- ol,3,7,11,15,19,23,27,31,35-nonamethyl-,(2E,- 6E,10E,14E,18E,22E,26E,30E)-;75%solanesol;
EINECS: 603-532-7
Density: 0.889 g/cm3
Melting Point: 33 °C
Boiling Point: 685.6 °C at 760 mmHg
Flash Point: 130.2 °C
Appearance: brown waxy solid
Safety: 24/25
PSA: 20.23000
LogP: 14.75690
Related products
Synthetic route

(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethyl-5-p-tolylsulphonylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-ol

13190-97-1

solanesol

Conditions
ConditionsYield
With lithium; ethylamine In diethyl ether at -78℃;50%
68690-45-9, 80370-68-9, 53254-63-0

(2E,6E)-3,7,11-trimethyl-1-(p-tolylsulfonyl)dodeca-2,6,10-triene

71135-48-3

(2E,6E,10E)-1-Benzyloxy-3,7,11-trimethyldodeca-2,6,10-trien-12-ol

70238-40-3

(2E,6E,10E)-2,6,10-trimethyl-12-(toluene-4-sulfonyl)-dodeca-2,6,10-trien-1-ol

13190-97-1

solanesol

Conditions
ConditionsYield
Multistep reaction;
...Expand
105-87-3

3,7-dimethyl-2E,6-octadien-1-yl acetate

13190-97-1

solanesol

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: 44 percent / SeO2 / aq. ethanol / 9 h / Heating
2: 72 percent / NaBH4 / methanol / 5 h / -10 °C
3: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
4: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
5: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C
6: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
7: 78 percent / dimethylformamide / 24 h / Ambient temperature
8: 1.) n-BuLi, 3.) H2O, KOH
9: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
10: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
11: 1.) n-BuLi, 3.) H2O, KOH
12: 70 percent / Li, ethylamine / diethyl ether
13: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
14: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 13 steps
1: 44 percent / SeO2 / aq. ethanol / 9 h / Heating
2: 72 percent / NaBH4 / methanol / 5 h / -10 °C
3: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
4: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
5: NaOMe / methanol / 2 h / Ambient temperature
7: 1.) n-BuLi, 3.) H2O, KOH
8: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
9: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
10: 1.) n-BuLi, 3.) H2O, KOH
11: 70 percent / Li, ethylamine / diethyl ether
12: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
13: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 15 steps
1: 44 percent / SeO2 / aq. ethanol / 9 h / Heating
2: 72 percent / NaBH4 / methanol / 5 h / -10 °C
3: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
4: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
5: NaOMe / methanol / 2 h / Ambient temperature
6: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C
7: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
8: 78 percent / dimethylformamide / 24 h / Ambient temperature
9: 1.) n-BuLi, 3.) H2O, KOH
10: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
11: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
12: 1.) n-BuLi, 3.) H2O, KOH
13: 70 percent / Li, ethylamine / diethyl ether
14: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
15: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
50848-64-1

2E,6E,10E-geranylgeranyl bromide

13190-97-1

solanesol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 78 percent / dimethylformamide / 24 h / Ambient temperature
2: 1.) n-BuLi, 3.) H2O, KOH
3: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
4: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
5: 1.) n-BuLi, 3.) H2O, KOH
6: 70 percent / Li, ethylamine / diethyl ether
7: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
8: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
37905-04-7

(2E,6E)-8-bromo-3,7-dimethylocta-2,6-dienyl acetate

13190-97-1

solanesol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
2: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C
3: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
4: 78 percent / dimethylformamide / 24 h / Ambient temperature
5: 1.) n-BuLi, 3.) H2O, KOH
6: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
7: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
8: 1.) n-BuLi, 3.) H2O, KOH
9: 70 percent / Li, ethylamine / diethyl ether
10: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
11: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 10 steps
1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
2: NaOMe / methanol / 2 h / Ambient temperature
4: 1.) n-BuLi, 3.) H2O, KOH
5: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
6: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
7: 1.) n-BuLi, 3.) H2O, KOH
8: 70 percent / Li, ethylamine / diethyl ether
9: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
10: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 12 steps
1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
2: NaOMe / methanol / 2 h / Ambient temperature
3: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C
4: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
5: 78 percent / dimethylformamide / 24 h / Ambient temperature
6: 1.) n-BuLi, 3.) H2O, KOH
7: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
8: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
9: 1.) n-BuLi, 3.) H2O, KOH
10: 70 percent / Li, ethylamine / diethyl ether
11: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
12: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 7 steps
1: 1.) n-BuLi, 3.) H2O, KOH
2: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
3: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
4: 1.) n-BuLi, 3.) H2O, KOH
5: 70 percent / Li, ethylamine / diethyl ether
6: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
7: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 4 steps
1: 1.) n-BuLi, 3.) H2O, KOH
2: 70 percent / Li, ethylamine / diethyl ether
3: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
4: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
37905-03-6

8-hydroxygeranyl acetate

13190-97-1

solanesol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
2: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
3: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C
4: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
5: 78 percent / dimethylformamide / 24 h / Ambient temperature
6: 1.) n-BuLi, 3.) H2O, KOH
7: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
8: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
9: 1.) n-BuLi, 3.) H2O, KOH
10: 70 percent / Li, ethylamine / diethyl ether
11: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
12: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 11 steps
1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
2: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
3: NaOMe / methanol / 2 h / Ambient temperature
5: 1.) n-BuLi, 3.) H2O, KOH
6: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
7: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
8: 1.) n-BuLi, 3.) H2O, KOH
9: 70 percent / Li, ethylamine / diethyl ether
10: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
11: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 13 steps
1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
2: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
3: NaOMe / methanol / 2 h / Ambient temperature
4: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C
5: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
6: 78 percent / dimethylformamide / 24 h / Ambient temperature
7: 1.) n-BuLi, 3.) H2O, KOH
8: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
9: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
10: 1.) n-BuLi, 3.) H2O, KOH
11: 70 percent / Li, ethylamine / diethyl ether
12: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
13: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 8 steps
1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
2: 1.) n-BuLi, 3.) H2O, KOH
3: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
4: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
5: 1.) n-BuLi, 3.) H2O, KOH
6: 70 percent / Li, ethylamine / diethyl ether
7: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
8: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 5 steps
1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
2: 1.) n-BuLi, 3.) H2O, KOH
3: 70 percent / Li, ethylamine / diethyl ether
4: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
5: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
37905-02-5

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate

13190-97-1

solanesol

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 72 percent / NaBH4 / methanol / 5 h / -10 °C
2: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
3: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
4: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C
5: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
6: 78 percent / dimethylformamide / 24 h / Ambient temperature
7: 1.) n-BuLi, 3.) H2O, KOH
8: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
9: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
10: 1.) n-BuLi, 3.) H2O, KOH
11: 70 percent / Li, ethylamine / diethyl ether
12: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
13: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 12 steps
1: 72 percent / NaBH4 / methanol / 5 h / -10 °C
2: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
3: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
4: NaOMe / methanol / 2 h / Ambient temperature
6: 1.) n-BuLi, 3.) H2O, KOH
7: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
8: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
9: 1.) n-BuLi, 3.) H2O, KOH
10: 70 percent / Li, ethylamine / diethyl ether
11: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
12: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 14 steps
1: 72 percent / NaBH4 / methanol / 5 h / -10 °C
2: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
3: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
4: NaOMe / methanol / 2 h / Ambient temperature
5: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C
6: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
7: 78 percent / dimethylformamide / 24 h / Ambient temperature
8: 1.) n-BuLi, 3.) H2O, KOH
9: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
10: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
11: 1.) n-BuLi, 3.) H2O, KOH
12: 70 percent / Li, ethylamine / diethyl ether
13: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
14: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
24034-73-9

Geranylgeraniol

13190-97-1

solanesol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
2: 78 percent / dimethylformamide / 24 h / Ambient temperature
3: 1.) n-BuLi, 3.) H2O, KOH
4: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
5: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
6: 1.) n-BuLi, 3.) H2O, KOH
7: 70 percent / Li, ethylamine / diethyl ether
8: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
9: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
53254-60-7

3,7-dimethyl-1-(p-toluenesulfonyl)-2(E),6-octadiene

13190-97-1

solanesol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
2: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C
3: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
4: 78 percent / dimethylformamide / 24 h / Ambient temperature
5: 1.) n-BuLi, 3.) H2O, KOH
6: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
7: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
8: 1.) n-BuLi, 3.) H2O, KOH
9: 70 percent / Li, ethylamine / diethyl ether
10: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
11: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 10 steps
1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
2: NaOMe / methanol / 2 h / Ambient temperature
4: 1.) n-BuLi, 3.) H2O, KOH
5: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
6: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
7: 1.) n-BuLi, 3.) H2O, KOH
8: 70 percent / Li, ethylamine / diethyl ether
9: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
10: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Multi-step reaction with 12 steps
1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
2: NaOMe / methanol / 2 h / Ambient temperature
3: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C
4: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
5: 78 percent / dimethylformamide / 24 h / Ambient temperature
6: 1.) n-BuLi, 3.) H2O, KOH
7: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
8: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
9: 1.) n-BuLi, 3.) H2O, KOH
10: 70 percent / Li, ethylamine / diethyl ether
11: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
12: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
24529-80-4

(E)-1-O-acetyl-4-chloro-3-methyl-2-buten-1-ol

13190-97-1

solanesol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
2: 50 percent / Li, ethylamine / diethyl ether / -78 °C
View Scheme
Raw Materials
37905-03-6
24529-80-4
37905-04-7
37905-02-5
53254-60-7
50848-64-1
24034-73-9
105-87-3
Downstream Products
5677-54-3
303-97-9
52610-77-2
523-39-7
303-98-0
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Chemistry

Molecular Formula: C45H74O
Molecular Weight: 631.07 g/mol
Index of Refraction: 1.506
Density: 0.889 g/cm3
Flash Point: 130.2 °C
Enthalpy of Vaporization: 114.99 kJ/mol
Boiling Point: 685.6 °C at 760 mmHg
Vapour Pressure: 9.21E-22 mmHg at 25 °C
Melting point: 33 °C
Storage tempreture: -20 °C
Appearance: Brown waxy solid
Structure of Solanesol (CAS NO.13190-97-1):
                      
Product Category of Solanesol (CAS NO.13190-97-1): Miscellaneous Natural Products;Nicotine Derivatives;Biochemistry;Terpenes;Natural Plant Extract

Uses

 Solanesol (CAS NO.13190-97-1) is ahigh molecular weight isoprenoid alcohol isolated from tobacco leaf.

Toxicity Data With Reference

RTECS : MP5366666

Specification

 Solanesol , its cas register number is 13190-97-1. It also can be called 3,7,11,15,19,23,27,31,35-Nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-ol .