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[ CAS No. 105-87-3 ] {[proInfo.proName]}

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Chemical Structure| 105-87-3
Chemical Structure| 105-87-3
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Emily Fryer ; Sujay Guha ; Lucero E. Rogel-Hernandez , et al. DOI: PubMed ID:

Abstract: Throughout history, humans have relied on plants as a source of medication, flavoring, and food. Plants synthesize large chemical libraries and release many of these compounds into the rhizosphere and atmosphere where they affect animal and microbe behavior. To survive, nematodes must have evolved the sensory capacity to distinguish plant-made small molecules (SMs) that are harmful and must be avoided from those that are beneficial and should be sought. This ability to classify chemical cues as a function of their value is fundamental to olfaction and represents a capacity shared by many animals, including humans. Here, we present an efficient platform based on multiwell plates, liquid handling instrumentation, inexpensive optical scanners, and bespoke software that can efficiently determine the valence (attraction or repulsion) of single SMs in the model nematode, Caenorhabditis elegans. Using this integrated hardware-wetware-software platform, we screened 90 plant SMs and identified 37 that attracted or repelled wild-type animals but had no effect on mutants defective in chemosensory transduction. Genetic dissection indicates that for at least 10 of these SMs, response valence emerges from the integration of opposing signals, arguing that olfactory valence is often determined by integrating chemosensory signals over multiple lines of information. This study establishes that C. elegans is an effective discovery engine for determining chemotaxis valence and for identifying natural products detected by the chemosensory nervous system.

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Product Details of [ 105-87-3 ]

CAS No. :105-87-3 MDL No. :MFCD00015037
Formula : C12H20O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 196.29 Pubchem ID :-
Synonyms :
NSC 2584;Geranyl ethanoate;Geraniol acetate
Chemical Name :(E)-3,7-Dimethylocta-2,6-dien-1-yl acetate

Calculated chemistry of [ 105-87-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.58
Num. rotatable bonds : 6
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 60.13
TPSA : 26.3 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.83
Log Po/w (XLOGP3) : 4.04
Log Po/w (WLOGP) : 3.24
Log Po/w (MLOGP) : 2.95
Log Po/w (SILICOS-IT) : 2.98
Consensus Log Po/w : 3.21

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.21
Solubility : 0.122 mg/ml ; 0.000622 mol/l
Class : Soluble
Log S (Ali) : -4.3
Solubility : 0.00993 mg/ml ; 0.0000506 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.52
Solubility : 0.597 mg/ml ; 0.00304 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.72

Safety of [ 105-87-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 105-87-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 105-87-3 ]

[ 105-87-3 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 105-87-3 ]
  • [ 37905-02-5 ]
YieldReaction ConditionsOperation in experiment
41% With selenium(IV) oxide; In ethanol; for 22h;Reflux; Geranyl acetate (7) (6.84 g, 34.9 mmol) pre-dissolved in 100 mL of 95% ethanol was added dropwise over 40 min to a refluxing solution of SeO2(5.8 g, 52 mmol) in 300 mL of 95% ethanol. The mixture was heated under reflux for 22 h. The black precipitate was removed by vacuum filtration over a pad of silica-gel, and washed with 95% ethanol. Solvent was removed at reduced pressure, and 400 mL of ethyl ether was added. Organic layer was washed with brine (4×80 mL), dried overNa2SO4, and concentrated under vacuum. The residue was purified byusing silica gel column chromatography to give a light yellow oil(2.8 g) with a yield of 41%.
24% In ethanol; Next, the carbon atom at position 8 was subjected to selenium oxidation in ethanol to obtain an aldehyde form (compound represented by (bii) below) (yield: 24%).
Example 8General Preparation of Lycophyll 2HCrocetindialdehyde (238) was obtained from SynChem, Inc. (Des Plaines, Ill.) as a brick-red solid and was used without further purification. Lycopene was obtained from ChromaDex (Santa Ana, Calif.) as a red solid and was used without further purification. Acetic acid 3,7-dimethyl-8-oxo-octa-2,6-dienyl ester (230a) (Liu and Prestwich 2002) was synthesized by literature procedures from commercially available geranyl acetate (228a). All other reagents and solvents used were purchased from Across Organics (Morris Plains, N.J.) and Sigma-Aldrich (St. Louis, Mo.) and were used without further purification. All reactions were performed under a nitrogen atmosphere. All flash chromatographic purifications were performed on Natland International Corporation 230-400 mesh silica gel using indicated solvents. LC/MS (APCI and ESI+modes) were recorded on an Agilent 1100 LC/MSD VL system; column: Zorbax Eclipse XDB-C18 Rapid Resolution (4.6×75 mm, 3.5 μm); temperature: 25'.C; flow rate: 1.0 mL/min.; mobile phase (A=0.025% TFA in H2O, B=0.025% TFA in acetonitrile). Gradient program (for intermediates 230a-236a and 216a): 70% A/30% B (start), step gradient to 50% B over 5 minutes, step gradient to 100% B over 1.3 minutes, hold at 100% B over 4.9 minutes. Gradient program (for intermediates 218a, 2H): 70% A/30% B (start), step gradient to 50% B over 5 minutes, step gradient to 98% B over 3.3 minutes, hold at 98% B over 16.9 minutes. All-trans lycophyll was obtained from crude material using a Waters 996 Photo Diode Array detector, Millipore 600E System Controller and Waters 717 Autosampler; column: YMC C30 Carotenoid S-5, (10×250 mm, 5 μm column); temperature: 25 C.; flow rate: 4.7 mL/min; mobile phase (A=methanol (MeOH), B=methyl-t-butyl ether (MTBE)) Gradient program: 60% A/40% B (start), step gradient to 80% A over 1 minute, hold at 80% A over 119 minutes. Fractions were collected from 55-66 minutes. Fraction analysis was performed on a YMC C30 Carotenoid S-5, (4.6×250 mm, 5 μm column). Proton nuclear magnetic resonance (NMR) spectra were obtained on a Varian Unity INOVA 500 spectrometer operating at 500.111 MHz (megahertz). Electronic absorption spectra were recorded on a Cary 50 Bio UV-Visible spectrophotometer.
With tert.-butylhydroperoxide; selenium(IV) oxide; In dichloromethane; water; for 48h; Procedure adapted from literature procedures.15 Selenium dioxide (0.742 g, 6.68 mmol, 14mol %) was suspended in 75 ml DCM in a 500 ml round bottom flask. tert-Butyl hydroperoxide (25 ml,186.8 mmol, 2 equiv.; Luperox 70 wt. % in H2O) was added and the reaction was stirred for 30 min generating a clear, biphasic solution. Geranial acetate (20 ml, 93.3 mmol; Alfa Aesar) was added via syringe. A reflux condenser was attached and the reaction was stirred for 48 h without heating. The reaction was diluted with 100 ml MeOH and cooled to 0 C. Sodium borohydride was added slowly until aldehyde not observed by TLC (Rf = 0.52 (2:1 Hex:EtOAc; KMnO4). Solution turned from clear to red toyellow to clear during this process. The reaction was diluted with another 100 ml DCM and 100 ml H2O
With tert.-butylhydroperoxide; selenium(IV) oxide; silica gel; salicylic acid; In dichloromethane; at 20℃; for 26h;Inert atmosphere; A suspension of selenium dioxide (5.6 mg, 1.0 mmol) tert-butyl hydroperoxide (0.24 mL, 2.5 mmol), salicylic acid (12 mol%, 16.6 mg) in anhydrous dichloromethane (20 mL) was stirred for 20 min at room temperature, and then silica gel (230-400 mesh, 72.0 mg) was added. After 30 min, the geranyl acetate 9 (196.3 mg,1.0 mmol) was slowly added. The mixture was stirred for 26 h, filtered through Celite, and washed with 10% potassium hydroxide and brine. The extract was dried over Na2SO4 and concentrated under vacuum. The resulting dark orange residue was dissolved in 4 mL of ethanol and cooled to 0 C, and sodium borohydride (37.8 mg, 1.0 mmol) was added in several portions. After 30 min, a saturated solution of NH4Cl (5 mL), brine, and ethyl acetate was added. The mixture was extracted with ethyl acetate and once with dichloromethane, dried, and concentrated. The residue was purified by flash chromatography eluting with hexane/AcOEt (9/1, v/v) to give alcohol 10 as a yellow oil (160.0 mg, 75%). 1H NMR (400 MHz, CDCl3): δ (ppm)5.38-5.28 (m, 2H), 4.55 (2H, d, J 7.2), 3.96 (2H, s), 2.28-2.06 (5H,m), 2.05 (3H, s), 1.70 (3H, s), 1.60 (3H, s).

Reference： [1]Organic Process Research and Development,2005,vol. 9,p. 830 - 836
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[5]Tetrahedron Letters,2019,vol. 60
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[9]Journal of the Chemical Society. Perkin transactions I,1981,p. 761 - 769
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[11]Biochimica et Biophysica Acta - General Subjects,2013,vol. 1830,p. 3635 - 3642
[12]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 351 - 361
[13]Patent: US2014/171675,2014,A1 .Location in patent: Paragraph 195-196
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[15]Tetrahedron,1974,vol. 30,p. 715 - 718
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[17]Journal of the American Chemical Society,1977,vol. 99,p. 5526 - 5528
[18]Journal of the Chemical Society. Chemical communications,1972,p. 486 - 487
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[27]Journal of Organic Chemistry,1999,vol. 64,p. 807 - 818
[28]Heterocycles,1998,vol. 47,p. 139 - 142
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[30]Journal of Organic Chemistry,1985,vol. 50,p. 3767 - 3774
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[33]Patent: US2008/221377,2008,A1 .Location in patent: Page/Page column 39; 19
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[38]Tetrahedron,2020,vol. 76
  • 2
  • [ 105-87-3 ]
  • [ 37905-03-6 ]
  • [ 37905-02-5 ]
YieldReaction ConditionsOperation in experiment
45%; 19% With selenium(IV) oxide; tert-butyl hydroperoxide; In dichloromethane; at 0℃; for 5h;Inert atmosphere; General procedure: Starting material (1.00 mmol) was added to a solution of selenium dioxide (44 mg, 0.40 mmol) and t-BuOOH (453 mg, 3.10 mmol) in dichloromethane (5 mL) at 0C. After stirring under nitrogen at 0C for a time t (vide infra), the mixture was diluted with ethyl acetate (15 mL), and washed successively with water (2 x 10 mL), saturated NaHCO3 (10 mL), water (10 mL) and brine (10 mL). The organic layer was then dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by chromatography on silica gel (hexanes / ethyl acetate).
With selenium(IV) oxide; In ethanol; for 1h;Reflux; SeO2 (4.34 g, 37.9 mmol) was added to a solution of geranyl acetate (Compound 29, 7.7 ml, 36 mmol) in EtOH (20 ml) at room temperature, and the mixture was refluxed for one hour. The reaction solution was allowed to warm to room temperature, and was filtered through celite. The filtrate was concentrated, and the residue was then subjected to column chromatography on silica gel (Hexane:EtOAc = 1:1). The fractions containing alcohol (Compound 30) and aldehyde (Compound 31) were collected. After evaporation of the solvent, the residue was dissolved in Et2O (100 ml). MnO2 (85% purity, 22.5 g, 220 mmol) was added to this solution followed by stirring for 15 hours. The reaction solution was filtered through celite, and the filtrate was washed with a saturated aqueous NaCl solution, and was dried over Na2SO4. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (Hexane:EtOAc = 4:1) to yield the aldehyde (Compound 31) (2.142 g, 28%).
  • 3
  • [ 105-87-3 ]
  • [ 57745-82-1 ]
  • [ 29210-77-3 ]
  • [ 98-55-5 ]
  • [ 69842-09-7 ]
  • 4
  • [ 115-95-7 ]
  • [ 78-70-6 ]
  • [ 106-25-2 ]
  • [ 106-24-1 ]
  • [ 141-12-8 ]
  • [ 105-87-3 ]
  • [ 98-55-5 ]
  • 5
  • [ 105-87-3 ]
  • E,E-2,6-dimethyl-2,6-octadiene-1,8-diol-8-acetate [ No CAS ]
  • [ 37905-02-5 ]
YieldReaction ConditionsOperation in experiment
35%; 25% With tert.-butylhydroperoxide; 1-butyl-3-methylimidazolium Tetrafluoroborate;selenium(IV) oxide; 3,4-Dihydroxybenzoic acid; In water; at 40 - 50℃; for 6h;Product distribution / selectivity; Into a 100 mL flask equipped with a magnetic rotor and a reflux condenser, 50 mg of selenium dioxide, 100 mg of 3,4-dihydroxybenzoic acid, 1 g of 1-butyl-3-methylimidazolium tetrafluoroborate and 0.5 g of 70 wt% aqueous tert-butylhydroperoxide were charged and the mixture was stirred and maintained for 30 minutes at an inner temperature of 40 oC. After that, 1.58 g of geranyl acetate was added to the mixture, and the resulting mixture was heated to an inner temperature of 50 oC. To the mixture, 2.2 g of 70 wt% aqueous tert-butylhydroperoxide was added dropwise over 1 hour at the same temperature with stirring. The resulting mixture was stirred to effect the reaction for 5 hours at the same temperature. After completion of the reaction, the reaction mixture was cooled to room temperature. 10 g of n-hexane was added to the reaction mixture and the extracting treatment was carried out to obtain a n-hexane phase and an ionic liquid phase. The ionic liquid phase was extracted two times by n-hexane and obtained n-hexane phase was mixed to the n-hexane phase obtained before to obtain an organic phase containing oxygen-containing compounds. 1.5 g of an ionic liquid phase containing 1-butyl-3-methylimidazolium tetrafluoroborate was obtained.Yield of each component E,E-2,6-dimethyl-2,6-octadiene-1,8-diol-8-acetate: 35 %, E,E-2-formyl-8-acetoxy-6-methyl-2,6-octadiene: 25 %, 33 % of the starting geranyl acetate was remained.
  • 6
  • [ 106-24-1 ]
  • [ 64-19-7 ]
  • [ 105-87-3 ]
  • [ 586-62-9 ]
  • [ 98-55-5 ]
  • [ 138-86-3 ]
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