Pro-xylane CAS#: 439685-79-7

By Christina Duan,
Structure of Pro-xylane CAS# 439685-79-7
IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名Pro-xylane
IUPAC Name(2S,3R,4S,5R)-2-(2-hydroxypropyl)oxane-3,4,5-triol 
分子结构Structure of Pro-xylane CAS# 439685-79-7
CAS编号 439685-79-7
别名Pro-xylane
439685-79-7
Hydroxypropyl tetrahydropyrantriol
Mexoryl SBB
Pro-xylane (pharmaceutical)
(2S,3R,4S,5R)-2-(2-hydroxypropyl)tetrahydro-2H-pyran-3,4,5-triol
4U3GMG1OT1
(2S,3R,4S,5R)-2-(2-hydroxypropyl)oxane-3,4,5-triol
UNII-4U3GMG1OT1
CHEMBL479843
SCHEMBL1660373
L-Gluco-octitol, 1,5-anhydro-6,8-dideoxy-, (7XI)-
DTXSID10196004
WLZ2819
KOGFZZYPPGQZFZ-QVAPDBTGSA-N
ER4017
AKOS040742450
DB13121
ER-4017
c-beta-d-xylopyranoside-2-hydroxypropane
TS-08006
HY-108036
CS-0027204
HYDROXYPROPYL TETRAHYDROPYRANTRIOL [INCI]
pro-xylane pound>>Hydroxypropyl tetrahydropyrantriol
Nano Liposomal HYDROXYPROPYL TETRAHYDROPYRANTRIOL
Q27260499
(2S,3R,4S,5R)-2-(2-hydroxypropyl)oxane-3,4,5-trio
L-GLUCO-OCTITOL, 1,5-ANHYDRO-6,8-DIDEOXY-, (7.XI.)-
分子式C8H16O5 
分子量192.21
InChIInChI=1S/C8H16O5/c1-4(9)2-6-8(12)7(11)5(10)3-13-6/h4-12H,2-3H2,1H3/t4?,5-,6+,7+,8+/m1/s1
InChI KeyKOGFZZYPPGQZFZ-QVAPDBTGSA-N
Isomeric SMILESCC(C[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O
Patent Information
Patent IDTitlePublication Date
WO2018/114850COSMETIC COMPOSITION COMPRISING ONE OR MORE POLAR OIL(S), A C2-C6 ALIPHATIC MONOALCOHOL AND A POLYOL, AT LEAST ONE HYDROPHILIC ACTIVE AGENT, AND COMPRISING LESS THAN 7% BY WEIGHT OF WATER 2018
WO2017/68068USE OF GLYCOSIDES TO INCREASE HAIR MASS2017
US2008/3191Composition combining a C-glycoside derivative and an emulsifying polymer2008
WO2008/4165USE OF C-GLYCOSIDE DERIVATIVES AS PRO-DESQUAMATING ACTIVE AGENTS2008

Physical Data

Appearance30% pro-xylane solution

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)
Chemical shifts, Spectrum1Hwater-d2
Chemical shifts1Hwater-d2
Spectrum13C
Chemical shifts, Spectrum13C
Chemical shifts1H

Route of Synthesis (ROS)

Route of Synthesis (ROS) of Pro-xylane CAS# 439685-79-7
Route of Synthesis (ROS) of Pro-xylane CAS# 439685-79-7
ConditionsYield
With Pd(OH)2/C; hydrogen In ethyl acetate at 20℃; under 620.594 Torr; Schlenk technique;

Experimental Procedure
1-6 Step c, Synthesis of Bosein (2S,3R,4S,5R)-2-(2-hydroxypropyl)tetrahydro-2H-pyran-3,4,5-triol:
Add 20% Pd(OH) to the Schlenk bottle2/C(30mg), replaced with nitrogen three times, vacuumed, the 1-((2S,3S,4S,5R)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2- Ethyl) propan-2-ol (3.0g, 6.5mmol) in ethyl acetate (30mL) was added to the Schlenk flask, reacted at room temperature under hydrogen (12psi) atmosphere for 10 hours, filtered, concentrated to obtain a syrupy (2S, 3R ,4S,5R)-2-(2-hydroxypropyl)tetrahydro-2H-pyran-3,4,5-triol (1.24g, yield 99%).		99%
With Pd/C; hydrogen

Experimental Procedure
(3)The benzyl group in the product obtained in step (2) is removed by catalytic hydrogenation with palladium carbon to obtain Bosein, (2S,3R,4S,5R)-2-(2-hydroxypropyl)tetrahydro-2H-pyran -3,4,5-triol.

Safety and Hazards

Pictogram(s)
Signal
GHS Hazard StatementsNot Classified
Precautionary Statement Codes

Other Data

Druglikeness
Lipinski rules component
分子量192.212
logP-1.202
HBA5
HBD4
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)90.15
Rotatable Bond (RotB)2
Matching Veber Rules2
Use Pattern
Anti-aging, promotes skin cell renewal, helps repair and rebuild the skin’s collagen and glycosaminoglycans, thereby reducing wrinkles and fine lines. Moisturizing and nourishing, promotes the synthesis of collagen, repairs damaged skin; enhances overall skin health.

(S)-Pro-xylane CAS#: 868156-46-1

By Christina Duan,
Structure of (S)-Pro-xylane CAS# 868156-46-1
IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名(S)-Pro-xylane
IUPAC Name
分子结构 Structure of (S)-Pro-xylane CAS# 868156-46-1
CAS编号 868156-46-1
EINECS Number
MDL NumberMFCD32701904
Beilstein Registry Number
别名
分子式C8H16O5
分子量192.210
InChI
InChI Key
Canonical SMILES
Patent Information
Patent IDTitlePublication Date
US2005/250708Novel C-glycosides, uses thereof2005

Physical Data

AppearanceSolid
Melting Point, °C
120 – 122

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)
Chemical shifts, Spectrum1Hwater-d2
Chemical shifts, Spectrum13Cwater-d2
Chemical shifts1H
Chemical shifts13C
Chemical shifts1HCD3OD

Route of Synthesis (ROS)

Route of Synthesis (ROS) of (S)-Pro-xylane CAS# 868156-46-1
Route of Synthesis (ROS) of (S)-Pro-xylane CAS# 868156-46-1
ConditionsYield
With sodium tris(acetoxy)borohydride In isopropyl alcohol at 20℃; Product distribution / selectivity;

Experimental Procedure
2 Production of C-β-D-xylopyranoside-2-(S)-hydroxypropane
EXAMPLE 2 Production of C-β-D-xylopyranoside-2-(S)-hydroxypropane The expected compound was obtained according the process described in Example 1, replacing the 2 ml of acetic acid and the sodium borohydride with two times 1.2 equivalents of sodium triacetoxyborohydride (NaBH(OAc)3). The product was obtained with a quantitative yield, and selectively in (β, S) form. The physico chemical characteristics are identical in all respects to those obtained in Example 1.		100%
With sodium tetrahydroborate; acetic acid In isopropyl alcohol at 20℃; for 1.5h; Product distribution / selectivity;

Experimental Procedure
1 Production of C-β-D-xylopyranoside-2-(S)-hydroxypropane
EXAMPLE 1 Production of C-β-D-xylopyranoside-2-(S)-hydroxypropane 2 ml of acetic acid, followed rapidly by 120 mg (1.2 eq.) of sodium borohydride as granules were added to a solution of 500 mg of C-β-D-xylopyranoside-2-propanone (described in Example 1 of application WO-02/051828) in 9 ml of isopropanol. The medium was left at ambient temperature for 30 minutes with stirring. 120 mg (1.2 eq.) of sodium borohydride as granules were then added. The reaction medium was left for 1 hour at ambient temperature with stirring. 10 ml of acetone were then added and, after stirring for 30 minutes at ambient temperature, the reaction medium was concentrated under vacuum. The residue obtained was purified by silica gel chromatography so as to selectively produce the expected compound C-β-D-xylopyranoside-2-(S)-hydroxypropane with a 95% yield. Physico chemical characteristics of the compound: Melting point: 120-122° C. Optical rotation: -37° (at 20° C. in methanol, and at a concentration [C]=1 g/100 ml) 1H NMR: 1.03 (t, 3H); 1.46 (m, 1H); 1.71 (m, 1H); 2.85 (m, 1H); 2.94 (m, 1H); 2.99 (m, 2H); 3.24 (m, 1H); 3.67 (m, 1H); 3.77 (m, 1H) Structure confirmed by X-ray diffraction.		95%

Safety and Hazards

Pictogram(s)
Signal
GHS Hazard StatementsNot Classified
Precautionary Statement Codes

Other Data

Druglikeness
Lipinski rules component
分子量192.212
logP-1.202
HBA5
HBD4
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)90.15
Rotatable Bond (RotB)2
Matching Veber Rules2
Use Pattern
Anti-aging, promotes skin cell renewal, helps repair and rebuild the skin’s collagen and glycosaminoglycans, thereby reducing wrinkles and fine lines. Moisturizing and nourishing, promotes the synthesis of collagen, repairs damaged skin; enhances overall skin health.