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Geraniol
Cas No: 106-24-1
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106-24-1 Usage

Description

Geraniol is a kind of monoterpenoid as well as alcohol. It is mainly existed in plant oils such as rose oil, palmarosa oil, and citronella oil. It can also be found in plants such as geraniums and lemongrass. It has a rose-like scent and is therefore used in perfumes as well as many kinds of flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, and blueberry. Another major application of geraniol is being used as an effective plant-based insect repellent for treatment of mosquitoes, house flies, stable flies, cockroaches, fire ants, fleas and lone star ticks. On the other hand, its scent can also attract bees.

References

https://en.wikipedia.org/wiki/Geraniol https://pubchem.ncbi.nlm.nih.gov/compound/geraniol#section=Top

Description

Geraniol has a characteristic rose-like odor. Geraniol may be prepared by fractional distillation from those essential oils rich in geraniol, or synthetically from myrcene; commercial geraniol cannot be classified according to its alcohol content, as most of the recurring impurities are alcoholic in nature (nerol, citronellol, tetrahydrogeraniol). Gas-chromatography techniques may be usefully employed to determine the geraniol content in a product.

Chemical Properties

Geraniol has a characteristic rose-like odor The physical constants vary for the various commercial products, depending on the total geraniol content; specifc gravity and refractive index may be indicative of the purity of the product Commercial geraniol cannot be classifed according to its alcohol content, as most of the recurring impurities are alcoholic in nature (nerol, citronellol, tetrahydrogeraniol) Gas chromatography techniques may be usefully employed to determine the gera- niol content in a product.

Chemical Properties

Geraniol occurs in nearly all terpene-containing essential oils, frequently as an ester. Palmarosa oil contains 70–85% geraniol; geranium oils and rose oils also contain large quantities. Geraniol is a colorless liquid, with a floral, rose-like odor. Since geraniol is an acyclic, doubly unsaturated alcohol, it can undergo a number of reactions, such as rearrangement and cyclization. Rearrangement in the presence of copper catalysts yields citronellal. In the presence of mineral acids, it cyclizes to form monocyclic terpene hydrocarbons, cyclogeraniol being obtained if the hydroxy function is protected. Partial hydrogenation leads to citronellol, and complete hydrogenation of the double bonds yields 3,7-dimethyloctan-l-ol (tetrahydrogeraniol). Citral may be obtained from geraniol by oxidation or by catalytic dehydrogenation. Geranyl esters are prepared by esterification. Geraniol is one of the most frequently used terpenoid fragrance materials. It can be used in all floral, rose-like compositions and does not discolor soaps. In flavor compositions, geraniol is used in small quantities to accentuate citrus notes. It is an important intermediate in the manufacture of geranyl esters, citronellol, and citral.

Chemical Properties

colourless to pale yellow liquid with an odour of roses

Occurrence

The presence of geraniol in nature has been reported in more than 160 essential oils: ginger grass, lemongrass, Ceylon and Java citronella, tuberose, oak musk, orris, champaca, ylang-ylang, mace, nutmeg, sassafras, Cayenne Bois-de-Rose, Acacia farnesiana, geramium clary sage, spike, lavandin, lavender, jasmine, coriander, carrot, myrrh, eucalyptus, lime, mandarin petitgrain, bergamot petitgrain, bergamot, lemon, orange and others The essential oils of palmarosa and Cymbopogon winterianus contain the highest levels of geraniol (approx 80 to 95%) Also reported in numerous other sources including apple juice, citrus peel oils and juices, bilberry, cranberry, other berries, guava, papaya, cinnamon, ginger, corn mint oil, mustard, nutmeg, mace, milk, coffee, tea, whiskey, honey, passion fruit, plums, mushrooms, mango, starfruit, cardamom, coriander leaf and seeds, litchi, Ocimum basilicum, myrtle leaf, rosemary, clary sage, Spanish sage and chamomile oil

Uses

Geraniol is used in the synthesis of insect repellant. It is also used in the synthesis of Angelicoin A and Herecinone J, which inhibit collagen-induced platelet aggregation.

Uses

Geraniol was used in field evaluation of synthetic herbivore-induced plant volatiles as attractants to beneficial insects.It was used to evaluate the tumor-suppressive potency of isoprenoids in vitro and in vivo.

Uses

geraniol is perfuming and with tonic properties. It is a primary constituent in many essential oils, including citronella, lavender, lemongrass, orange flower, and ylang-ylang.

Definition

ChEBI: A monoterpenoid consisting of two prenyl units linked head-to-tail and functionalised with a hydroxy group at its tail end.

Preparation

A convenient route for the production of geraniol and nerol consists of the hydrogenation of citral, which is used in large quantities as an intermediate in the synthesis of vitamin A. Large-scale processes have, therefore, been developed for producing geraniol. Currently, these are far more important than isolation from essential oils. Nevertheless, some geraniol is still isolated from essential oils for perfumery purposes. 1) Isolation from essential oils: Geraniol is isolated from citronella oils and from palmarosa oil. Fractional distillation of, for example, Java citronella oil (if necessary, after saponification of the esters present) yields a fraction containing about 60% geraniol, as well as citronellol and sesquiterpenes. Aproductwith a higher geraniol content and slightly different odor quality for use in fine fragrances is obtained by fractionating palmarosa oil after saponification of the geranyl esters. 2) Synthesis from β-pinene: Pyrolysis of β-pinene yields myrcene, which is converted into a mixture of predominantly geranyl, neryl, and linalyl chloride by addition of hydrogen chloride in the presence of small amounts of catalyst, for example, copper(I) chloride and an organic quaternary ammonium salt. After removal of the catalyst, the mixture is reacted with sodium acetate in the presence of a nitrogen base (e.g., triethylamine) and converted to geranyl acetate, neryl acetate, and a small amount of linalyl acetate.Geraniol is obtained after saponification and fractional distillation of the resulting alcohols. 3) Synthesis from linalool: A 96% pure synthetic geraniol prepared by isomerization of linalool has become commercially available. Orthovanadates are used as catalysts, to give a >90% yield of a geraniol–nerol mixture. Geraniol of high purity is finally obtained by fractional distillation. A considerable portion of commercially available geraniol is produced by a modified process: linalool obtained in a purity of about 65% from α-pinene is converted into linalyl borates, which rearrange in the presence of vanadates as catalysts to give geranyl and neryl borates. The alcohols are obtained by hydrolysis of the esters. 4) Synthesis from citral: Citral has very recently come to be produced petrochemically in very large quantities, so partial hydrogenation of citral has become a very economical route for the production of geraniol. A high selectivity for this reaction can be achieved by the use of special catalysts [106] or by special reaction techniques.

Aroma threshold values

Detection: 4 to 75 ppb.

Taste threshold values

Taste characteristics at 10 ppm: sweet foral rose, citrus with fruity, waxy nuances.

General Description

Colorless to pale yellow oily liquid with a sweet rose odor.

Reactivity Profile

An unsaturated aliphatic hydrocarbon and an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Anticancer Research

Starting from antitumor activity against several cell lines by an arrest occurring atthe G0/G1 cell cycle and ultimately with an increase of apoptosis, this molecule wasfound to interfere with the mevalonic cycle enzyme. Suppression of prenylation ofproteins leads to the inhibition of DNA synthesis, and the suppression of 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) leads to a reduction of the mevalonate pool andthus limits protein isoprenylation. In the same way, a reduction of cholesterol biodisponibilitywas controlled (Pattanayak et al. 2009; Ni et al. 2012; Dahham et al.2016).

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion, subcutaneous, and intramuscular routes. A severe human skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Chemical Synthesis

By fractional distillation from those essential oils rich in geraniol, or synthetically from myrcene.

Metabolism

Geraniol is metabolized in the rabbit by ω-oxidation and by reduction of an α β-unsaturated bond (Parke, 1968). The products of geraniol metabolism are 'Hildebrandt acid' and 7-carboxy-3-methylocta-6-enoic acid. The latter acid is optically active (Williams, 1959).

Purification Methods

Purify geraniol by ascending chromatography or by thin layer chromatography on plates of kieselguhr G with acetone/water/liquid paraffin (130:70:1) as solvent system. Hexane/ethyl acetate (1:4) is also suitable. Also purify it by GLC on a silicone-treated column of Carbowax 20M (10%) on Chromosorb W (60-80 mesh). [Porter Pure Appl Chem 20 499 1969.] Store it in full, tightly sealed containers in the cool and protect from light. It has a pleasant odour. [cf p 681, Beilstein 1 IV 2277.]
InChI:InChI=1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+

106-24-1 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (G0027)  Geraniol  >96.0%(GC) 106-24-1 25mL 110.00CNY Detail
TCI America (G0027)  Geraniol  >96.0%(GC) 106-24-1 100mL 330.00CNY Detail
TCI America (G0027)  Geraniol  >96.0%(GC) 106-24-1 500mL 715.00CNY Detail
Alfa Aesar (A13736)  Geraniol, 97%    106-24-1 50g 240.0CNY Detail
Alfa Aesar (A13736)  Geraniol, 97%    106-24-1 250g 692.0CNY Detail
Alfa Aesar (A13736)  Geraniol, 97%    106-24-1 1000g 2276.0CNY Detail
Sigma-Aldrich (48798)  Geraniol  analytical standard 106-24-1 48798-1ML 1,485.90CNY Detail
Sigma-Aldrich (48798)  Geraniol  analytical standard 106-24-1 48798-5ML 3,621.15CNY Detail

106-24-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name geraniol

1.2 Other means of identification

Product number -
Other names (E)-3,7-Dimethylocta-2,6-dien-1-ol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:106-24-1 SDS

106-24-1Synthetic route

3,7-dimethyl-2,6-octadienal
141-27-5

3,7-dimethyl-2,6-octadienal

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With phosphotungstic acid; sodium tetrahydroborate In methanol100%
With sodium tetrahydroborate; sodium hydroxide In water at 35℃; for 0.416667h; pH=12; Reagent/catalyst; Green chemistry;99%
antimony(III) chloride; aluminium In water; N,N-dimethyl-formamide for 1h; Ambient temperature;98%
3,7-dimethylocta-2,6-dien-1-yl ethanoate
16409-44-2

3,7-dimethylocta-2,6-dien-1-yl ethanoate

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With potassium carbonate In methanol Inert atmosphere;100%
3,7-dimethyl-2E,6-octadien-1-yl acetate
105-87-3

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

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With potassium carbonate In methanol at 25℃; for 0.166667h;99%
With methanol at 80℃; for 6h; Inert atmosphere; Schlenk technique;99%
With methanol; oxo[hexa(trifluoroacetato)]tetrazinc for 12h; Reflux; Inert atmosphere;96%
(2E)-3,7-dimethyl-1-triphenylmethoxy-2,6-octadiene
92464-82-9

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

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With naphthalene; lithium In tetrahydrofuran at -78℃; for 1.5h;99%
geranyl 2-tetrahydropyranyl ether
59632-99-4

geranyl 2-tetrahydropyranyl ether

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With dimethylbromosulphonium bromide In methanol; dichloromethane at 20℃; for 2h;98%
Nafion-H In methanol for 6h;97%
With lithium perchlorate at 55℃; Product distribution; acid catalyst generated by electrolysis;96%
geraniol tert-butyldimethylsilyl ether
80873-81-0

geraniol tert-butyldimethylsilyl ether

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With Decaborane In tetrahydrofuran; methanol at 20℃; for 1h;98%
With iron(III) chloride In methanol at 20℃; for 0.5h;96%
With iron(III) p-toluenesulfonate hexahydrate In methanol at 20℃; for 2.25h; chemoselective reaction;86%
{[(2E)-3.7-dimethyl-2,6-octadien-1-yl]oxy}(triethyl)silane
160882-63-3

{[(2E)-3.7-dimethyl-2,6-octadien-1-yl]oxy}(triethyl)silane

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
10percent Pd/C In methanol at 20℃; for 2h;98%
C25H32O3
1204225-79-5

C25H32O3

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With ethanol; copper(ll) bromide at 20℃; for 0.5h;98%
O-(trans-3,7-dimethylocta-2,6-dien-1-yl)trimethylsilane
72106-90-2

O-(trans-3,7-dimethylocta-2,6-dien-1-yl)trimethylsilane

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
Tetrabutyl-1,3-diisothiocyanato-distannoxane In methanol for 16h; Ambient temperature;95%
1,3-di(NCS)-tetrabutyldistannoxane In methanol for 16h; Ambient temperature; Deprotection of silyl ethers;95%
With water; aluminium In hexane for 0.0833333h; Ambient temperature;90%
(E)-3,7-dimethyl-1-(2-phenylallyloxy)-2,6-octadiene

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

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h;95%
ethyl (E)-3,7-dimethylocta-2,6-dienoate
32659-21-5

ethyl (E)-3,7-dimethylocta-2,6-dienoate

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With diisobutylaluminium hydride In hexane at -70 - 10℃;92%
With diisobutylaluminium hydride In tetrahydrofuran72%
With lithium aluminium tetrahydride Yield given;
With diisobutylaluminium hydride In tetrahydrofuran at -78 - 22℃; for 3h; Inert atmosphere;
With diisobutylaluminium hydride In diethyl ether; hexane at -78℃; for 3h; Inert atmosphere;
geranyl benzyl ether
52188-73-5

geranyl benzyl ether

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With lithium; ethylenediamine In tetrahydrofuran at -10℃; for 3.33333h;92%
2-{(E)-2-[((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-dimethyl-silanyl]-vinyl}-phenol
152753-75-8

2-{(E)-2-[((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-dimethyl-silanyl]-vinyl}-phenol

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
In acetonitrile for 0.5h; Irradiation;91%
(2R,3R)-2-((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-3-heptadecafluorooctyl-tetrahydro-pyran

(2R,3R)-2-((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-3-heptadecafluorooctyl-tetrahydro-pyran

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With methanol; toluene-4-sulfonic acid In tetrahydrofuran at 70℃; for 24h; deprotection of alcoholic OH;91%
3-{(E)-2-[((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-diisopropyl-silanyl]-vinyl}-naphthalen-2-ol
342890-05-5

3-{(E)-2-[((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-diisopropyl-silanyl]-vinyl}-naphthalen-2-ol

A

Geraniol
106-24-1

Geraniol

B

2,2-diisopropyl-2H-1-oxa-2-sila-anthracene

2,2-diisopropyl-2H-1-oxa-2-sila-anthracene

Conditions
ConditionsYield
In methanol for 0.75h; Irradiation;A 90%
B 91%
3,7-dimethyl-1-[tris(trimethylsilyl)silyl]-2,6-octadien-1-ol

3,7-dimethyl-1-[tris(trimethylsilyl)silyl]-2,6-octadien-1-ol

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With methanol In dichloromethane at 10℃; for 0.5h; Product distribution; Irradiation;90%
In methanol; dichloromethane desilylation; Photolysis;90%
2-((E)-3,7-Dimethyl-octa-2,6-dienyloxymethyl)-1,3-dimethyl-benzene

2-((E)-3,7-Dimethyl-octa-2,6-dienyloxymethyl)-1,3-dimethyl-benzene

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With lithium; ethylenediamine In tetrahydrofuran at -10℃; for 2h;88%
1-(1-geranyloxy)-1-(2-nitrophenyl)-2,4-hexadiene

1-(1-geranyloxy)-1-(2-nitrophenyl)-2,4-hexadiene

A

Geraniol
106-24-1

Geraniol

B

2-Methyl-2,4a-dihydro-[1,2]oxazino[2,3-a]indol-5-one

2-Methyl-2,4a-dihydro-[1,2]oxazino[2,3-a]indol-5-one

Conditions
ConditionsYield
In methanol for 1.75h; Decomposition; Irradiation;A 84%
B 60%
(E)-1-(1-((3,7-dimethylocta-2,6-dien-1-yl)oxy)methyl)-4-methoxybenzene
82529-81-5

(E)-1-(1-((3,7-dimethylocta-2,6-dien-1-yl)oxy)methyl)-4-methoxybenzene

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water for 1h; Ambient temperature;81.9%
With lithium; ethylenediamine In tetrahydrofuran at -10℃; for 4h;55%
With dimethylsulfide; magnesium bromide In dichloromethane for 8h; Ambient temperature;35%
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide for 72h; Inert atmosphere; Glovebox; UV-irradiation;10%
(E)-Geranyl chloroacetate
60758-60-3

(E)-Geranyl chloroacetate

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 0 - 20℃; Inert atmosphere;80%
2-{(E)-2-[((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-diisopropyl-silanyl]-vinyl}-phenol
152753-81-6

2-{(E)-2-[((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-diisopropyl-silanyl]-vinyl}-phenol

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
In acetonitrile for 0.5h; Irradiation;75%
{[(2E)-3.7-dimethyl-2,6-octadien-1-yl]oxy}(triethyl)silane
160882-63-3

{[(2E)-3.7-dimethyl-2,6-octadien-1-yl]oxy}(triethyl)silane

A

3,7-dimethyl-2,6-octadienal
141-27-5

3,7-dimethyl-2,6-octadienal

B

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With water; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 0.75h;A 73.6%
B 24.4%
1-((E)-3,7-Dimethyl-octa-2,6-dienyloxymethoxy)-4-methoxy-benzene
124068-38-8

1-((E)-3,7-Dimethyl-octa-2,6-dienyloxymethoxy)-4-methoxy-benzene

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile at 0℃; for 0.5h; Product distribution; different reagents, times, solvents, temperatures and catalyst;73%
(E)-1-(((3,7-dimethylocta-2,6-dien-1-yl)oxy)methyl)-2-methoxybenzene
1426824-93-2

(E)-1-(((3,7-dimethylocta-2,6-dien-1-yl)oxy)methyl)-2-methoxybenzene

A

Geraniol
106-24-1

Geraniol

B

2-methylmethoxybenzene
578-58-5

2-methylmethoxybenzene

Conditions
ConditionsYield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide for 72h; Inert atmosphere; Glovebox; UV-irradiation;A 73%
B 23%
1-hydroxy-3-phenylsulfinylmethyl-7-methylocta-2Z,6-diene
112766-85-5

1-hydroxy-3-phenylsulfinylmethyl-7-methylocta-2Z,6-diene

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With ammonia; sodium In diethyl ether at -70℃; for 0.0833333h;72%
Nerol
106-25-2

Nerol

A

3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

B

Geraniol
106-24-1

Geraniol

C

terpineol
98-55-5

terpineol

Conditions
ConditionsYield
With bis-trimethylsilanyl peroxide; bis(acetylacetonate)oxovanadium In dichloromethane at 25℃; for 7h;A 70%
B 11%
C 3%
bis(acetylacetonate)oxovanadium; bis-trimethylsilanyl peroxide In dichloromethane at 25℃; for 7h;A 70 % Chromat.
B 11 % Chromat.
C 3 % Chromat.
bis(acetylacetonate)oxovanadium; bis-trimethylsilanyl peroxide In dichloromethane at 25℃; for 7h; Product distribution;A 70 % Chromat.
B 11 % Chromat.
C 3 % Chromat.
geranyl benzyl ether
52188-73-5

geranyl benzyl ether

A

Geraniol
106-24-1

Geraniol

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With bis(acetylacetonate)oxovanadium; methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate at 120℃; for 48h;A 63%
B 69%
1-phenylsulfonyl-2-methyl-4-hydroxy-but-2-ene
59830-37-4

1-phenylsulfonyl-2-methyl-4-hydroxy-but-2-ene

3-methyl-2-butenylmagnesium chloride
35189-96-9

3-methyl-2-butenylmagnesium chloride

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
copper acetylacetonate In tetrahydrofuran for 18h; Ambient temperature;65%
2,3,6,7-tetrabromo-3,7-dimethyl-octan-1-ol
87378-16-3

2,3,6,7-tetrabromo-3,7-dimethyl-octan-1-ol

Geraniol
106-24-1

Geraniol

Conditions
ConditionsYield
With sodium sulfide; Aliquat 336 In water; benzene for 1h; Ambient temperature;64%
Geraniol
106-24-1

Geraniol

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With hydrogen; aluminum oxide; copper In isopropyl alcohol at 90℃; for 12h;100%
With hydrogen; polymer-supported rhodium catalyst In dichloromethane under 1551.49 Torr; for 10h; Hydrogenation;96%
With 1,1'-bis(diphenylphosphino)ferrocene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; Butane-1,4-diol; potassium tert-butylate at 110℃; for 24h; Inert atmosphere;71%
Geraniol
106-24-1

Geraniol

acetic anhydride
108-24-7

acetic anhydride

3,7-dimethyl-2E,6-octadien-1-yl acetate
105-87-3

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

Conditions
ConditionsYield
With pyridine Ambient temperature;100%
With pyridine In tetrahydrofuran at 0 - 20℃; Acetylation;100%
With pyridine; dmap at 20℃; for 1h; Acetylation;99%
Geraniol
106-24-1

Geraniol

trans-geranyl bromide
6138-90-5

trans-geranyl bromide

Conditions
ConditionsYield
With phosphorus tribromide In diethyl ether at 0℃; for 2h;100%
With phosphorus tribromide In diethyl ether at 0℃; for 0.166667h;100%
With titanium(IV) bromide; N-methylaniline In dichloromethane at -23℃; for 1h;100%
Geraniol
106-24-1

Geraniol

1-chloro-3,7-dimethylocta-2,6-diene
5389-87-7

1-chloro-3,7-dimethylocta-2,6-diene

Conditions
ConditionsYield
With titanium tetrachloride; N-methylaniline In dichloromethane at -23℃; for 1h;100%
With chloro-trimethyl-silane; potassium carbonate In Petroleum ether at 0℃; for 2h;97%
With dmap; triethylamine; p-toluenesulfonyl chloride In dichloromethane for 3h; Ambient temperature;97%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

Geraniol
106-24-1

Geraniol

geranyl 2-tetrahydropyranyl ether
59632-99-4

geranyl 2-tetrahydropyranyl ether

Conditions
ConditionsYield
bis(trimethylsilyl)sulphate In dichloromethane; 1,2-dichloro-ethane at 0℃; for 0.25h;100%
With toluene-4-sulfonic acid In dichloromethane for 3h; Ambient temperature;99.5%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃;99%
Geraniol
106-24-1

Geraniol

[3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl]methanol
50727-94-1

[3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl]methanol

Conditions
ConditionsYield
With tetrahexylammonium tetrakis(diperoxomolybdo)phosphate In chloroform at 40℃; for 7h;100%
With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium In chlorobenzene at 80℃; for 5h;100%
With tetrabutylphosphonium peroxotantalate; dihydrogen peroxide In water at 0℃; for 3.5h; Schlenk technique; regioselective reaction;100%
Geraniol
106-24-1

Geraniol

(2S,3S)-2,3-epoxygeraniol
82188-73-6

(2S,3S)-2,3-epoxygeraniol

Conditions
ConditionsYield
With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve In dichloromethane at -23℃; for 2h;100%
With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate In dichloromethane at -40℃; for 5h; Sharpless Asymmetric Epoxidation; Inert atmosphere; enantioselective reaction;99%
With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane at -25 - -20℃; Molecular sieve;98%
Geraniol
106-24-1

Geraniol

3,7-dimethyl-2,6-octadienal
141-27-5

3,7-dimethyl-2,6-octadienal

Conditions
ConditionsYield
With manganese(IV) oxide In hexane at 0℃; for 6h;100%
With manganese(IV) oxide100%
With manganese(IV) oxide In hexane at 0℃; for 6h; Product distribution; also with activated MnO2, other substrates;100%
Geraniol
106-24-1

Geraniol

diethyl chlorophosphate
814-49-3

diethyl chlorophosphate

(E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate
60699-32-3

(E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate

Conditions
ConditionsYield
With pyridine In diethyl ether at -15 - 20℃;100%
In pyridine at 0 - 20℃; for 1h;98%
With pyridine In diethyl ether at -15 - 20℃; for 3h;94%
Geraniol
106-24-1

Geraniol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

geraniol tert-butyldimethylsilyl ether
80873-81-0

geraniol tert-butyldimethylsilyl ether

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;100%
With 1H-imidazole In N,N-dimethyl-formamide99%
With 1H-imidazole In N,N-dimethyl-formamide98%
Geraniol
106-24-1

Geraniol

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(E)-tert-butyl[(3,7-dimethylocta-2,6-dien-1-yl)oxy]diphenylsilane
139109-03-8, 117638-12-7

(E)-tert-butyl[(3,7-dimethylocta-2,6-dien-1-yl)oxy]diphenylsilane

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 0.25h; Ambient temperature;100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h; Silylation;100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h;100%
Geraniol
106-24-1

Geraniol

(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol
40036-54-2

(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol

Conditions
ConditionsYield
With tert.-butylhydroperoxide In acetonitrile at 80℃; for 24h; Catalytic behavior; Reagent/catalyst;100%
With urea hydrogen peroxide adduct; methyltrioxorhenium(VII) In dichloromethane at 20℃; for 0.25h;73%
Stage #1: Geraniol With N-Bromosuccinimide; dimethyl sulfoxide at 10℃; for 0.5h; Inert atmosphere;
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 0℃; for 0.5h; Inert atmosphere;
60%
vinyl acetate
108-05-4

vinyl acetate

Geraniol
106-24-1

Geraniol

3,7-dimethyl-2E,6-octadien-1-yl acetate
105-87-3

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

Conditions
ConditionsYield
With dilithium tetra(tert-butyl)zincate In toluene at 0℃; for 1h; Inert atmosphere;100%
With N,N'-bismesityl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 1h;99%
1,3-bis(2,4,6-trimethyl-phenyl)imidazol-2-ylidene In tetrahydrofuran at 20℃; for 1h;99%
Geraniol
106-24-1

Geraniol

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

(E)-3,7-dimethylocta-2,6-dien-1-yl 3-phenylpropanoate

(E)-3,7-dimethylocta-2,6-dien-1-yl 3-phenylpropanoate

Conditions
ConditionsYield
[Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In toluene at 150℃; for 16h;100%
Geraniol
106-24-1

Geraniol

phenyl isocyanate
103-71-9

phenyl isocyanate

(E)-3,7-dimethylocta-2,6-dien-1-yl phenylcarbamate
57706-89-5

(E)-3,7-dimethylocta-2,6-dien-1-yl phenylcarbamate

Conditions
ConditionsYield
With MoCl2O2(dmf)2 In dichloromethane at 20℃; for 0.333333h;100%
In pyridine at 5 - 20℃; for 12h;88%
Stage #1: Geraniol; phenyl isocyanate In toluene for 1h; Heating;
Stage #2: With 5-hydroxymethyl-2-norbornene In toluene Heating;
Stage #3: With [{1,3-bis(mesyl)imidazolidin-2-yl}RuCl2(PCy3)(=CHPh)] In dichloromethane for 0.5h; Heating; Further stages.;
78%
Geraniol
106-24-1

Geraniol

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

(E)-3,7-dimethylocta-2,6-dien-1-yl 3-phenylpropanoate

(E)-3,7-dimethylocta-2,6-dien-1-yl 3-phenylpropanoate

Conditions
ConditionsYield
With [Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 10h;100%
Stage #1: 3-Phenylpropionic acid With iodine; triphenylphosphine In dichloromethane at 20℃; for 0.166667h;
Stage #2: With gadolinium(III) trifluoromethanesulfonate In dichloromethane at 50℃; for 0.5h;
Stage #3: Geraniol In dichloromethane
71%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
Geraniol
106-24-1

Geraniol

(E)-geranyl-H-phosphinic acid
701279-14-3

(E)-geranyl-H-phosphinic acid

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); 9,9-dimethyl-4,6-bis(diphenylphosphino)xanthene; hypophosphorous acid In N,N-dimethyl-formamide at 85℃;100%
With hypophosphorous acid; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 85℃;
Geraniol
106-24-1

Geraniol

C11H20O2

C11H20O2

Conditions
ConditionsYield
With tert.-butylhydroperoxide In chloroform for 4h; Catalytic behavior; Reflux;100%
Geraniol
106-24-1

Geraniol

acetic acid
64-19-7

acetic acid

3,7-dimethyl-2E,6-octadien-1-yl acetate
105-87-3

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

Conditions
ConditionsYield
With Candida antarctica lipase B at 50℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction;99.9%
With hydroquinone at 120℃; Temperature; Reagent/catalyst;99.2%
With 1,3-propanesultone; N-ethyl-N-methylbutan-1-amine; toluene-4-sulfonic acid at 110℃; for 2h; Temperature; Reagent/catalyst;97%
Geraniol
106-24-1

Geraniol

butyric acid
107-92-6

butyric acid

Geranyl butyrate
106-29-6

Geranyl butyrate

Conditions
ConditionsYield
With Candida antarctica lipase B at 50℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction;99.9%
With sodium hydroxide at 80℃; for 8h;66.94%
In hexane at 30℃; for 72h; Corynebacterium sp. S-401;23%
Geraniol
106-24-1

Geraniol

propionic acid
802294-64-0

propionic acid

geranyl propionate
105-90-8

geranyl propionate

Conditions
ConditionsYield
With Candida antarctica lipase B at 50℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction;99.6%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 23℃; for 0.5h;90%
In hexane at 30℃; for 72h; Corynebacterium sp. S-401;13%
In water at 30℃; for 18h; lipase from Aspergillus niger; Yield given;
With candida antarctica B (CALB) lipase immobilized in polyurethane (PU) foam Enzymatic reaction;
(phenylthio)acetic acid chloride
7031-27-8

(phenylthio)acetic acid chloride

Geraniol
106-24-1

Geraniol

3,7-dimethyl-2(E),6-octadienyl (phenylthio)acetate
87519-21-9

3,7-dimethyl-2(E),6-octadienyl (phenylthio)acetate

Conditions
ConditionsYield
With pyridine In dichloromethane for 3h;99.3%
Geraniol
106-24-1

Geraniol

pivaloyl chloride
3282-30-2

pivaloyl chloride

(E)-3,7-dimethylocta-2,6-dien-1-yl pivalate
85796-37-8

(E)-3,7-dimethylocta-2,6-dien-1-yl pivalate

Conditions
ConditionsYield
With pyridine; 1H-imidazole at 20℃; for 1h;99%
With pyridine In dichloromethane at 20℃; for 2h; Inert atmosphere;96%
With pyridine In dichloromethane at 20℃; for 2h; Inert atmosphere;96%
Geraniol
106-24-1

Geraniol

3-methylbut-3-enoyl chloride
3350-77-4

3-methylbut-3-enoyl chloride

(E)-geranyl 3-methyl-3-butenoate
84825-22-9

(E)-geranyl 3-methyl-3-butenoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78℃; for 3h;99%
With pyridine In diethyl ether for 1.5h;86%
Geraniol
106-24-1

Geraniol

(+/-)-2,3-epoxygeraniol
62960-04-7

(+/-)-2,3-epoxygeraniol

Conditions
ConditionsYield
With tert.-butylhydroperoxide; V(IV)O(salen derivative) In carbon dioxide; water at 45℃; under 165487 Torr; for 48h;99%
With dihydrogen peroxide; W2O11(2-)*2Ph3PCH2Ph(1+) In 1,2-dichloro-ethane at 0℃; for 24h;98%
With tert.-butylhydroperoxide; chromium silicalite-2 In methanol at 65℃; for 5h;95%
Geraniol
106-24-1

Geraniol

benzoyl chloride
98-88-4

benzoyl chloride

(E)-geranyl benzoate
94-48-4

(E)-geranyl benzoate

Conditions
ConditionsYield
With pyridine; dmap In diethyl ether for 20h; Inert atmosphere; Schlenk technique;99%
Stage #1: Geraniol; benzoyl chloride In dichloromethane at 20℃;
Stage #2: With poly{trans-bicyclo[2.2.1]hept-5-ene-2,3-di(chlorocarbonyl)} In dichloromethane Heating;
94%
With pyridine; dmap In diethyl ether for 2h; Ambient temperature; Yield given;
Geraniol
106-24-1

Geraniol

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

methyl (E)-3-{[(E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}acrylate

methyl (E)-3-{[(E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}acrylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane99%
With tributylphosphine In dichloromethane for 0.05h; Ambient temperature;91%
3,3-Dimethylacryloyl chloride
3350-78-5

3,3-Dimethylacryloyl chloride

Geraniol
106-24-1

Geraniol

(E)-geranyl 3-methyl-3-butenoate
84825-22-9

(E)-geranyl 3-methyl-3-butenoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78℃; for 3h;99%

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