[ CAS No. 5208-93-5 ] {[proInfo.proName]}

Name: 5208-93-5|3-Methyl-1-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-1,4-dien-3-ol|95%
Brand: Ambeed
SKU: A464240
Price: 10.0 USD
Availability: InStock
Rating: 93 (25 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 5208-93-5 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 5208-93-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5208-93-5 ]

SDS Specification

Alternatived Products of [ 5208-93-5 ]

Product Details of [ 5208-93-5 ]

CAS No. :	5208-93-5	MDL No. :	MFCD09751288
Formula :	C₁₅H₂₄O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PZGYHDPZANRCSM-PKNBQFBNSA-N
M.W :	220.35	Pubchem ID :	6436846
Synonyms :

Calculated chemistry of [ 5208-93-5 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.6
Num. rotatable bonds :	3
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	71.62
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.26
Log Po/w (XLOGP3) :	3.54
Log Po/w (WLOGP) :	4.01
Log Po/w (MLOGP) :	3.46
Log Po/w (SILICOS-IT) :	4.11
Consensus Log Po/w :	3.67

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.24
Solubility :	0.127 mg/ml ; 0.000578 mol/l
Class :	Soluble
Log S (Ali) :	-3.65
Solubility :	0.0494 mg/ml ; 0.000224 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.07
Solubility :	0.187 mg/ml ; 0.000847 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	4.24

Safety of [ 5208-93-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H227-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 5208-93-5 ]

* 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.

Upstream synthesis route of [ 5208-93-5 ]
Downstream synthetic route of [ 5208-93-5 ]

[ 5208-93-5 ] Synthesis Path-Upstream 1~1

1
[ 79-77-6 ]
[ 1826-67-1 ]
[ 5208-93-5 ]

Reference： [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 32, p. 7265 - 7272

[ 5208-93-5 ] Synthesis Path-Downstream 1~12

2
[ 116-11-0 ]
[ 5208-93-5 ]
[ 1196448-69-7 ]

Yield	Reaction Conditions	Operation in experiment
	phosphoric acid; In acetone; at -20 - 0℃;Inert atmosphere;	A mixture of 18.4 g of vinyl-beta-ionol (0.081 MoI) and 23.1 g of IPM (0.309 MoI) was stirred (magnetic stirrer) in a 250ml 3-neck round bottomed flask under argon at a Ti = -200C (Tj = ca. -25 0C). 0.0438 g of catalyst solution (H3PO4 18.1 w% in acetone, 0.081 mMol = 0.1 Mol% relative to vinyl-beta-ionol) were added at once with the help of a volume adjustable pipette with disposable tip. This clear and colorless solution was stored for 72 hours in a freezer at Ti = 0C. Out of the deep-freeze the solution was set basic with 34mul of thethylamine and stirred until room temperature was reached. The reaction mixture was then concentrated on a rota- vapor with a membrane-pump (10 mbar) and degassed with a high-vacuum pump (0.02 mbar on pump). During this process and the following work-up the temperature of the vinyl-beta-ionol-IPM-adduct should not exceed 22-25C. 22.8 g of crude product were isolated, containing 65 area% vinyl-beta-ionol-IPM-adduct, yield <n="13"/>62.3 %. Final purification was achieved in accordance with the method described above. The product could be isolated in 54.7% yield (15 g, 87% purity).Formula Molecular formula C19H32O2Monoisotopic mass 292.44Chemical name (CAS) 2-[(E)-3-(1 -Methoxy-1 -methyl-ethoxy)-3-methyl-penta- 1 ,4-dienyl]-1 ,3,3-thmethyl-cyclohexene1H-NMR (CDCI3) delta in ppm: 0.92 (6H, s, H-7 + H-8), 1.39-1.37 (2H, m, H-1 + H-6), 1.35 (3H, s, H-20 or H-21 ), 1.36 (3H, s, H-20 or H- 21 ), 1.44 (3H, s, H-15), 1.57-1.49 (2H, m, H-1 + H-6), 1.60 (3H, d, 4J = 0.75 Hz, H-9), 1.90 (2H, br t, 3J = 5.88 Hz, H-5), 3.17 (3H, s, H-19), 4.97 (1 H, dd, 3J =10.74 Hz; 5J = 1.40 Hz, H-14Z), 5.13 (1 H, dd, 3J = 17.65 Hz; 5J = 1.40 Hz, H-14E), 5.53 (1 H, d, 3J = 16.30 Hz, H-11 ), 5.93 (1 H, dd, 3J = 16.30 Hz; 5J = 0.94 Hz, H-10), 6.03 (1 H, dd, 3J = 10.74 Hz; 3J = 17.65 Hz, H-13).13, C-NMR (CDCI3) delta in ppm: 143.4 (C-13), 138.5 (C-11 ), 136.1 (C-3), 127.2 (C-4),124.6 (C-10), 110.9 (C-14), 100.3 (C-12), 76.8 (C-17),47.2 (C-19), 38.5 (C-1 or C-6), 33.3 (C-2), 31 .7 (C-5), 27.8 (C-7 + C-8), 26.3-25.2 (C-20 + C-21 ), 20.3 (C-9),18.3 (C-1 or C-6). <n="14"/>NMR parameter:NMR spectra were recorded on a Bruker Avance 300 spectrometer equipped with 5 mm BBO BB-1 H probe head operating at 300 MHz for 1H and 75.5 MHz for 13C. Spectra were recorded in CDCI3 and referenced to TMS (5H) or solvent signals (deltac): deltaH 0.00 / deltac 77.0. Assignments were based on 1H and 13C-NMR spectral data taking into account coupling constants and chemical shifts.

Reference： [1]Patent: WO2009/138389,2009,A1 .Location in patent: Page/Page column 11-13

3
[ 5208-93-5 ]
[ 67777-14-4 ]

Yield	Reaction Conditions	Operation in experiment
43.2%		Analogously to example 11, <strong>[5208-93-5]vinylionol</strong> in DMF or NMP was reacted firstly with tBuOOH. The resulting reaction was then further reacted in accordance with the details in table 2 with a base to give the end product of the formula I (R?H). The yields are given in table 2:

Reference： [1]Patent: US2013/116473,2013,A1 .Location in patent: Paragraph 0119

4
[ 5208-93-5 ]
[ 67777-14-4 ]
[ 1432964-99-2 ]

Yield	Reaction Conditions	Operation in experiment
46.6%; 5.9%	With tert.-butylhydroperoxide; copper(II) acetylacetonate hydrate; In pyridine; water; at 40℃; for 10.0h;	1 to 2 mol % of the metal salt/complex given in the table below were introduced into 1.5 g (6.8 mmol) of <strong>[5208-93-5]vinylionol</strong>, and 2.92 g (22.7 mmol) of 70% strength aqueous tert-BuOOH solution in 2.7 g (34.1 mmol) of pyridine were metered in in 3 portions at a rate in each case of 1 ml/min. The mixtures were then stirred for 10 h at 40 C. and analyzed for the formation of the compound I (R?H) and compound III (R?H) in the manner described above. The results are summarized in table 1 below.

Reference： [1]Patent: US2013/116473,2013,A1 .Location in patent: Paragraph 0118

5
[ 5208-93-5 ]
[ 1432965-26-8 ]
[ 1432965-13-3 ]

Reference： [1]Patent: US2013/116473,2013,A1
[2]Patent: US2013/116473,2013,A1
[3]Patent: US2013/116473,2013,A1

6
[ 5208-93-5 ]
[ 84592-32-5 ]

Reference： [1]Patent: US2013/116473,2013,A1
[2]Patent: US2013/116473,2013,A1
[3]Patent: US2013/116473,2013,A1

7
[ 75-91-2 ]
[ 5208-93-5 ]
[ 67777-14-4 ]
[ 1432964-99-2 ]

Yield	Reaction Conditions	Operation in experiment
16.9%; 42.8%	With cobalt(II) bromide; In pyridine; water; at 40℃; for 10.0h;	1 to 2 mol % of the metal salt/complex given in the table below were introduced into 1.5 g (6.8 mmol) of <strong>[5208-93-5]vinylionol</strong>, and 2.92 g (22.7 mmol) of 70% strength aqueous tert-BuOOH solution in 2.7 g (34.1 mmol) of pyridine were metered in in 3 portions at a rate in each case of 1 ml/min. The mixtures were then stirred for 10 h at 40 C. and analyzed for the formation of the compound I (R?H) and compound III (R?H) in the manner described above. The results are summarized in table 1 below.

Reference： [1]Patent: US2013/116473,2013,A1 .Location in patent: Paragraph 0118

8
[ 5208-93-5 ]
[ 6399-81-1 ]
[3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)penta-2,4-dien-1-yl]triphenylphosphanium bromide [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7265 - 7272

9
[ 79-77-6 ]
[ 1826-67-1 ]
[ 5208-93-5 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7265 - 7272

10
[ 5208-93-5 ]
C₂₃H₃₂O₂ [ No CAS ]
C₂₃H₃₂O₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7265 - 7272

11
[ 5208-93-5 ]
[ 603-35-0 ]
[ 1062-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; at 53℃; under 150015.0 Torr; for 1.5h;Autoclave; Inert atmosphere;	(1) After the high pressure reactor was leak-detected, (134.9 g, 0.51 mol) of triphenylphosphine and (49.3 g, 38 wt%, 0.51 mol) of hydrochloric acid were added thereto; after replacing with CO2 for 3 times, the autoclave was charged. CO2 gas and start stirring, The temperature was raised so that the temperature in the autoclave was 53 C, and the pressure in the autoclave was maintained at 20 MPa through a pressure regulating valve, and (110 g, 0.5 mol) of vinyl-beta ionol was pumped into the autoclave through a parallel flow pump to form a salt reaction. Preparation of C15 phosphonium salt. (2) After the salt formation reaction for 1.5 hours, (80.2 g, 0.56 mol) of C5 aldehyde was added to the autoclave through a parallel flow pump. (32.4 g) of [Bmim]Im ionic liquid and (810 g) solvent water, then venting pressure to release CO2, and mixing the materials uniformly. An alkali solution (26 g, that is, 0.65 mol of sodium hydroxide and 100 g of water) was added to the kettle to carry out a Wittig reaction. After Wittig reaction at 43 C for 2 h, the solid phase (triphenylphosphine oxide) and the filtrate phase (aqueous phase and n-hexane phase) were separated by suction filtration. The solid phase was washed with 50 mL of n-hexane; The obtained washing liquid and the filtrate phase (aqueous phase and n-hexane phase) are mixed and transferred to a separating funnel to be statically phase-separated to obtain a n-hexane solution phase of vitamin A acetate and water containing [Bmim]Im ionic liquid. phase. The aqueous phase containing the [Bmim]Im ionic liquid can be used directly for the next reaction without any post-treatment operation. N-hexane phase was evaporated to give a yellow oil after removal of the solvent under vacuum rotation 45C, to this yellow oil was added 450g 95% ethanol, Stir at 30 C, add 10 g of activated carbon, stir at 30 C for 30 minutes, filter while hot, the filtrate is cooled to -5 C, and kept for 5 hours. After filtration, 152.8 g of vitamin A acetate was obtained; after HPLC analysis, it was confirmed that vitamin A acetate was obtained, and the purity was calculated to be 99.74%, and the yield was 92.92%.

Reference： [1]Patent: CN109651150,2019,A .Location in patent: Paragraph 0060-0083

12
[ 5208-93-5 ]
[ 618-41-7 ]
[ 50464-14-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	In water; at 40℃;Microwave irradiation;	110g of vinyl beta-ionol,75g of benzenesulfinic acid and 500g of water were added to a 1000ml three-necked flask.Turn on the stirring to make the material evenly dispersed. Set the peristaltic pump flow to 40ml / min,Set the reaction temperature to 40 C, start the microwave generator,The microwave reactor shown in FIG. 3 was continuously pumped into the microwave reactor for microwave reaction.The material is collected at the discharge port and cooled to room temperature, filtered, and the filter cake is rinsed with 50g of water and then dried.Dry under vacuum at 40 C for 3h.Yielded 170.3 g of C15 sulfone(Ie 3-methyl-1- (benzenesulfonyl) -5- (2,6,6-trimethyl-1-cyclohexenyl) -2,4-pentadiene), the yield was 99.0%, The content is 99.3%.

Reference： [1]Patent: CN110272368,2019,A .Location in patent: Paragraph 0017-0019

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Ghs Precautionary Statements

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 5208-93-5 ] {[proInfo.proName]}

Quality Control of [ 5208-93-5 ]

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[ 5208-93-5 ] Synthesis Path-Upstream 1~1

[ 5208-93-5 ] Synthesis Path-Downstream 1~12

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Alkenes

Aliphatic Cyclic Hydrocarbons

Alcohols

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[ 5208-93-5 ]