There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Structure of 1-O-Hexadecyl-sn-glycerol
CAS No.: 506-03-6

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

Synonyms: (S)-1-O-HDG; (S)-HXDG

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

{[proInfo.pro_purity]}

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

Change View

Size

Price

VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock

{[ item.pr_size ]}{[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]}

Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

{[ item.pr_size ]}
{[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

Quality Control of [ 506-03-6 ] Purity: 97% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 506-03-6 ]

CAS No. :	506-03-6
Formula :	C₁₉H₄₀O₃
M.W :	316.52
SMILES Code :	O[C@@H](CO)COCCCCCCCCCCCCCCCC
Synonyms :	(S)-1-O-HDG; (S)-HXDG
English Name :	(S)-3-(Hexadecyloxy)propane-1,2-diol
MDL No. :	MFCD00151171

Safety of [ 506-03-6 ]

GHS Pictogram:
Signal Word:
Hazard Statements:
Precautionary Statements:
Class:
UN#:
Packing Group:

Application In Synthesis of [ 506-03-6 ]

* 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 [ 506-03-6 ]

[ 506-03-6 ] Synthesis Path-Downstream 1~14

1
[ 506-03-6 ]
[ 76-83-5 ]
[ 92471-46-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With dmap In pyridine at 100℃; for 3h;
78%	With triethylamine In tetrahydrofuran for 20h; Ambient temperature;
	In pyridine at 100℃; for 12h;	I 1-Hexadecyloxy-3-trityloxy-2-propanol (or D-ALLE) or 3-Hexadecyloxy-1-trityloxy-2-propanol (for L-ALLE) (compound II) 1-Hexadecyloxy-glycerol (for D-ALLE) or 3-Hexadecyloxy-glycerol (for L-ALLE) (7.9 grams), triphenylchloromethane (8.4 grams) and dry pyridine (40 ml) were heated at 100° C. for 12 hours. After cooling, 300 ml of ether and 150 ml of ice-cold water were added, and the reaction mixture was transferred to a separatory funnel. The organic phase was washed consecutively with 50 ml of ice water, 1% potassium carbonate solution (until basic) and 50 ml of water, then dried over anhydrous sodium sulfate. The solvent was evaporated, the residue was dissolved in 150 ml of warm petroleum ether and the resulting solution was cooled at 4° C. over night. After filtration of the precipitate, the filtrate was evaporated and the residue was recrystallized from 20 ml of ethyl acetate at -30° C., yielding 8.2 grams of 1-Hexadecyloxy-3-trityloxy-2-propanol (for D-ALLE) or 3-hexadecyloxy-1-trityloxy-2-propanol (for L-ALLE) (compound II, FIG. 1), melting point 49° C.

With triethylamine In tetrahydrofuran; acetonitrile for 17h; Reflux;

1 20 grams of (5)-l-hexadecyl- glycerol and 21.29 grams of triphenylchloromethane were dissolved in 369 ml dry tetrahydrofuran (THF) and 93 ml dry acetonitrile. 17.75 ml triethylamine was added and the reaction mixture was refluxed for 17 hours. The reaction mixture was cooled to room temperature, poured on ice (100 grams), transferred to a separatory funnel and extracted with methyl tert-butyl ether. The organic phase was washed consecutively with 200 ml water, twice with 200 ml dilute (1.5 %) sulfuric acid, 200 ml water, 200 ml saturated aqueous sodium bicarbonate, and again with 200 ml water. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to give 36.86 grams of crude product as a residue. This residue was dissolved in hot hexane (200 ml) and the resulting solution was cooled at 4 0C overnight. The precipitated product was filtered, yielding 30.71 grams of (i?)-l-hexadecyl-3-trityl-glycerol.

References: [1]Ohno; Fujita; Nakai; Kobayashi; Inoue; Nojima [Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 2, p. 572 - 582].
[2]Jakob; Brezesinski; Raith; Wolf; Dobner; Nuhn [Pharmazie, 1999, vol. 54, # 7, p. 545 - 546].
[3]Current Patent Assignee: VASCULAR BIOGENICS - US2003/225035, 2003, A1 Location in patent: Page 16.
[4]Current Patent Assignee: VASCULAR BIOGENICS - WO2010/52718, 2010, A1 Location in patent: Page/Page column 57.

2
[ 119879-76-4 ]
[ 506-03-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; Ambient temperature;

References: [1]Guivisdalsky, Pedro N.; Bittman, Robert [Journal of Organic Chemistry, 1989, vol. 54, # 19, p. 4637 - 4642].

3
[ CAS Unavailable ]
[ 506-03-6 ]

Yield	Reaction Conditions	Operation in experiment
	With boron trifluoride methanol complex In dichloromethane at 40℃; for 0.166667h; Yield given;

References: [1]Kleuser, Burkhard; Schmidt, Norbert; Gercken, Guenther [Chemistry and Physics of Lipids, 1993, vol. 66, # 1-2, p. 111 - 122].

4
[ 506-03-6 ]
[ 14470-28-1 ]
[ 118658-21-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	In tetrahydrofuran; pyridine for 2h; Ambient temperature;
	In tetrahydrofuran; pyridine; chloroform; ethyl acetate	94 (R)-1-(Hexadecyloxy)-3-[(4-methoxyphenyl)diphenylmethoxy]-2-propanol EXAMPLE 94 (R)-1-(Hexadecyloxy)-3-[(4-methoxyphenyl)diphenylmethoxy]-2-propanol To a solution of 15.34 g of (S)-3-(hexadecyloxy)-1,2-propanediol in 50 ml of pyridine is added dropwise with stirring a solution of 20.96 g of p-methoxytrityl chloride in 30 ml of tetrahydrofuran. Stirring is continued at ambient temperature for 2 hours followed by refrigeration for 18 hours. The mixture is filtered and the cake washed with ether. The combined filtrates are evaporated to a residue which is dissolved in chloroform and washed with 10% sodium bicarbonate and water then dried and evaporated to an oil which is purified by high pressure liquid chromatography on silica gel using 1:9 ethyl acetate:hexanes to give 28.44 g of the desired product as an oil.
	With pyridine; dmap at 20℃;

References: [1]Boeckel, C. A. A. van; Marel, G. A. van der; Westerduin, P.; Boom, J. H. van [Synthesis, 1982, # 5, p. 399 - 402].
[2]Kumar; Bhakuni [Tetrahedron Letters, 1993, vol. 34, # 21, p. 3463 - 3466].
[3]Current Patent Assignee: AMERICAN CYANAMID INC - US5144045, 1992, A.
[4]Carlin, Aaron F.; Beadle, James R.; Clark, Alex E.; Gully, Kendra L.; Moreira, Fernando R.; Baric, Ralph S.; Graham, Rachel L.; Valiaeva, Nadejda; Leibel, Sandra L.; Bray, William; McMillan, Rachel E.; Freshman, Jonathan E.; Garretson, Aaron F.; McVicar, Rachael N.; Rana, Tariq; Zhang, Xing-Quan; Murphy, Joyce A.; Schooley, Robert T.; Hostetler, Karl Y. [Journal of Medicinal Chemistry, 2023, vol. 66, # 8, p. 5802 - 5819].

5
[ 91326-86-2 ]
[ 506-03-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With hydrogenchloride In tetrahydrofuran Ambient temperature;
74%	With Amberlite IR-120 Plus In ethanol for 20h; Ambient temperature;
75 % Turnov.	With acetic acid In water for 3h; Heating;

	With trifluoroacetic acid
1.17 g	With water; acetic acid	2 4.1.6. General procedure for the synthesis of compounds14a-14c General procedure: 2,3-O-Isopropylidene-sn-glycerol (500.0 mg, 3.8 mmol) was added to a 50% aqueous solution of NaOH (8 mL). The reaction mixture was heated at 80 °C, before the addition of the n-alkyl bromide (15.2 mmol) and Bu4NBr (245.0 mg, 0.76 mmol). After disappearance of the starting materials (2 h), the reaction mixture was cooled and extracted with CH2Cl2. The organic solution was washed with water, brine, dried over Na2SO4, concentrated and purified by column chromatography (petroleum ether, then 20:1 petroleum ether/ethyl acetate) to give the 1-O-n-alkyl-2,3-O-isopropylidene-sn-glycerol. The 1-O-n-alkyl-2,3-O-isopropylidene-sn-glycerol was dissolved in 80% aqueous AcOH (1 mmol/5 mL). The mixture was stirred overnight at room temperature and then evaporated to dryness in vacuo. The residue was purified by column chromatography (3:1 petroleum ether/acetone) to afford the 1-O-n-alkyl-sn-glycerol.
	With hydrogenchloride In methanol for 15h; Reflux;	1.2. General procedure for the synthesis of alkylglycerols (5a-5o) General procedure: The synthesis of the AKGs was performed following the literature with some modifications (Baumann and Mangold 1964; Hanus et al. 2001; Appendino et al. 2003; Parkkari et al. 2006). LiAlH4 (550 mg, 14.5 mmol) was added slowly to a solution of the corresponding methyl ester (3.4 mmol) in anhydrous tetrahydrofuran (15 mL) at 0°C and stirred for 1 h and was then left at 20°C for 20 h. The reaction mixture was washed with NaOH (10%) followed by HCl (10%) and extracted with diethyl ether (3 × 20 mL); the extract was neutralized with saturated NaHCO3, dried under reduced pressure and purified by CC. The alcohol obtained was subsequently mesylated in absolute pyridine (4.5 mL, 55.6 mmol) at 0°C by the addition of MsCl (880 mg, 7.65 mmol) and the solution was maintained for 24 h at 20°C. After quenching the reaction with 5 mL of degasified water, the solution was extracted with diethyl ether (4 × 20 mL). The organic phase was washed with H2SO4 (2 N), neutralized, concentrated in vacuo, and the crude mesylate was purified by CC. KOH (127 mg, 2.26 mmol) was added to the chiral precursor (R)-solketal (283 mg, 2.14 mmol) in anhydrous toluene (2 mL). The reaction stirred at 50°C for 1 h before the addition of metallic Na (3 mg, 0.15 mmol) followed by the mesylate dissolved in toluene (15 mL), and the resulting mixture was kept at 50°C for 72 h. The reaction was quenched with HCl (10%) and extracted with ethyl ether (4 × 20 mL). The organic phase was neutralized, concentrated and purified by CC to give 1-O-alkyl-2,3-O-isopropylidene-sn-glycerol. This intermediate was deprotected in 5 mL of HCl:MeOH (1:10 v/v) and refluxed overnight. After the addition of H2O (10 mL) and extraction with diethyl ether (4 × 20 mL), the organic phase was neutralized, evaporatedto dryness in vacuo, and the residue was purified by CC to afford pure AKGs. Each step in the synthesis was monitored by TLC, and all CC steps were eluted with hexane-toluene-ethyl acetate (10:0:0-0:10:0-0:0:10) mixtures. The structures of the synthesised compounds were confirmed by 1H, 13C APT NMR with COSY, HMQC, HMBC and ESI-MS or HRESI-MS spectra along with the specific optical rotation.
63.6 %	With water; toluene-4-sulfonic acid In tetrahydrofuran; methanol at 20℃;	2 Specific experimental method: Take a 100mL eggplant-shaped bottle,add p-toluenesulfonic acid hydrate (220mg, 1.12mmol),raw material 16 (2.577g, 6.69mmol),methanol (40mL), tetrahydrofuran (10mL),water (0.35mL), ultrasonically dissolve until the mixed solution becomes clear,then the reaction solution is placed at room temperature to react,TLC plate monitors the reaction throughout the process until the raw material 16 reacts completely.Ammonia water is then added to quench the reaction,the solvent is removed and concentrated by rotary evaporator to obtain a crude product,column chromatography separation and purification (cyclohexane: acetone = 1:1),obtain compound 17.(white flakes, 1468mg, yield 63.6%)

References: [1]Ohno; Fujita; Nakai; Kobayashi; Inoue; Nojima [Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 2, p. 572 - 582].
[2]Mikkilineni, Amarendra B.; Kumar, Praveen; Abushanab, Elie [Journal of Organic Chemistry, 1988, vol. 53, # 26, p. 6005 - 6009].
[3]Guella, Graziano; Mancini, Ines; Pietra, Francesco [Helvetica Chimica Acta, 1987, vol. 70, p. 1050 - 1062].
[4]Yashunsky, Dmitry V.; Borodkin, Vladimir S.; Ferguson, Michael A. J.; Nikolaev, Andrei V. [Angewandte Chemie - International Edition, 2006, vol. 45, # 3, p. 468 - 474].
[5]Ni, Guanghui; Li, Zhiyuan; Liang, Kangjiang; Wu, Ting; De Libero, Gennaro; Xia, Chengfeng [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 11, p. 2966 - 2973].
[6]Fernández Montoya, Deicy J.; Contreras Jordan, Luis A.; Moreno-Murillo, Bárbara; Silva-Gómez, Edelberto; Mayorga-Wandurraga, Humberto [Natural Product Research, 2021, vol. 35, # 15, p. 2544 - 2550].
[7]Current Patent Assignee: SUN YAT SEN UNIVERSITY CHINA - CN118184695, 2024, A Location in patent: Paragraph 0117; 0123-0127.

6
[ 506-03-6 ]
[ 586-76-5 ]
[ 256440-35-4 ]

Yield	Reaction Conditions	Operation in experiment
0.7 mg	With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 25℃; for 3.5h;

References: [1]Aoki, Shunji; Higuchi, Kouichi; Kato, Ai; Murakami, Nobutoshi; Kobayashi, Motomasa [Tetrahedron, 1999, vol. 55, # 52, p. 14865 - 14870].

7
[ 849589-89-5 ]
[ 506-03-6 ]

Yield	Reaction Conditions	Operation in experiment
0.297 g	With pyridine; methanol In dichloromethane; pentane at 0 - 20℃; for 0.333333h;
0.297 g	With pyridine In methanol; dichloromethane; pentane at 20℃; for 0.333333h;

References: [1]Stamatov, Stephan D.; Stawinski, Jacek [Tetrahedron Letters, 2005, vol. 46, # 10, p. 1601 - 1605].
[2]Stamatov, Stephan D.; Stawinski, Jacek [Organic and Biomolecular Chemistry, 2007, vol. 5, # 23, p. 3787 - 3800].

8
[ 506-03-6 ]
[ 994-30-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In dichloromethane