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Chemical Structure| 56-45-1 Chemical Structure| 56-45-1
Chemical Structure| 56-45-1

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H-Ser-OH is a non-essential amino acid that plays a crucial role in cell proliferation.

Synonyms: Serine; (S)-Serine; L-Serine

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Product Details of L-Serine

CAS No. :56-45-1
Formula : C3H7NO3
M.W : 105.09
SMILES Code : O=C(O)[C@@H](N)CO
Synonyms :
Serine; (S)-Serine; L-Serine
MDL No. :MFCD00064224
InChI Key :MTCFGRXMJLQNBG-REOHCLBHSA-N
Pubchem ID :5951

Safety of L-Serine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of L-Serine

* 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 [ 56-45-1 ]
  • Downstream synthetic route of [ 56-45-1 ]

[ 56-45-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 67-56-1 ]
  • [ 56-45-1 ]
  • [ 7691-28-3 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With bromic acid; potassium bromide; sodium nitrite In water at -10 - 20℃;
Stage #2: With bromic acid In water at 65℃; for 48 h;
[1496] Step 2: methyl 2-bromo-3-hydroxypropanoate[1497] To a solution of L-serine (5.0 g, 47.6 mmol), a 48 w/wpercent bromic acid solution (13.0 mL, 109.5 mmol), and potassium bromide (20.0 g, 157.1 mmol) in water (44.0 mL) was added portionwise sodium nitrite (6.0 g, 80.9 mmol) at -10 ℃. The reaction mixture was stirred at room temperature overnight. The reaction mixture was saturated with sodium chloride and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated. The residue was dissolved in methanol (50.0 mL) and then 48 w/wpercent bromic acid (0.2 mL) was added thereto. The reaction mixture was stirred at 65 ℃ for 2 days and then concentrated under reduced pressure to discard excess methanol. The resulting dark yellow residue was dissolved in dichloromethane (100.0 mL) and then washed with a saturated sodium hydrogen carbonate solution (50.0 mL) and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and then evaporated. The residue was dried under reduced pressure to give 5.7 g of the titled compound (Yield: 65percent).[1498] 1H NMR (CDCl3, 400 MHz) δ 4.36(t, 1H), 4.01-4.08(m, 1H), 3.93-3.97(m, 1H), 3.82(s, 3H), 2.56(t, 1H)
65%
Stage #1: With bromic acid; potassium bromide; sodium nitrite In water at -10 - 20℃;
Stage #2: at 65℃; for 48 h;
Step 2:
methyl 2-bromo-3-hydroxypropanoate
To a solution of L-serine (5.0 g, 47.6 mmol), a 48 w/w percent bromic acid solution (13.0 mL, 109.5 mmol), and potassium bromide (20.0 g, 157.1 mmol) in water (44.0 mL) was added portionwise sodium nitrite (6.0 g, 80.9 mmol) at -10° C.
The reaction mixture was stirred at room temperature overnight.
The reaction mixture was saturated with sodium chloride and then extracted with ethyl acetate.
The organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated.
The residue was dissolved in methanol (50.0 mL) and then 48 w/w percent bromic acid (0.2 mL) was added thereto.
The reaction mixture was stirred at 65° C. for 2 days and then concentrated under reduced pressure to discard excess methanol.
The resulting dark yellow residue was dissolved in dichloromethane (100.0 mL) and then washed with a saturated sodium hydrogen carbonate solution (50.0 mL) and brine.
The organic layer was dried over anhydrous sodium sulfate, filtered, and then evaporated.
The residue was dried under reduced pressure to give 5.7 g of the titled compound (Yield: 65percent).
1H NMR (CDCl3, 400 MHz) δ 4.36 (t, 1H), 4.01-4.08 (m, 1H), 3.93-3.97 (m, 1H), 3.82 (s, 3H), 2.56 (t, 1H)
References: [1] Patent: WO2013/43001, 2013, A1, . Location in patent: Paragraph 1496; 1497; 1498.
[2] Patent: US2015/11528, 2015, A1, . Location in patent: Paragraph 0818-0819.
  • 2
  • [ 56-45-1 ]
  • [ 108-98-5 ]
  • [ 34317-61-8 ]
References: [1] Journal of the American Chemical Society, 1993, vol. 115, # 4, p. 1264 - 1270.
 

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