Ginsenoside Rg1

Iupac Name：(2R,3R,4S,5S,6R)-2-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

CAS No.: 22427-39-0

Molecular Weight：801.01300

Modify Date.: 2023-02-13 22:17

Introduction:

Ginsenoside Rg1 is one of the major active components of ginseng. Ginsenoside Rg1 displays promising effects by reducing cerebral Aβ levels. Ginsenoside Rg1 also reduces NF-κB nuclear translocation.

Ginsenoside Rg1 is a ginsenoside found in Panax ginseng and Panax japonicus var. major that is dammarane which is substituted by hydroxy groups at the 3beta, 6alpha, 12beta and 20 pro-S positions, in which the hydroxy groups at positions 6 and 20 have been converted to the corresponding beta-D-glucopyranosides, and in which a double bond has been introduced at the 24-25 position. It has a role as a neuroprotective agent and a pro-angiogenic agent. It is a 12beta-hydroxy steroid, a beta-D-glucoside, a tetracyclic triterpenoid, a ginsenoside and a 3beta-hydroxy-4,4-dimethylsteroid. It derives from a hydride of a dammarane.|Ginsenosides are a class of steroid glycosides, and triterpene saponins, found exclusively in the plant genus Panax (ginseng). Ginsenosides have been the target of research, as they are viewed as the active compounds behind the claims of ginseng's efficacy. Because ginsenosides appear to affect multiple pathways, their effects are complex and difficult to isolate. Rg1 Appears to be most abundant in Panax ginseng (Chinese/Korean Ginseng). It improves spatial learning and increase hippocampal synaptophysin level in mice, plus demonstrates estrogen-like activity.

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1. Names and Identifiers

: 1.1 Name; Ginsenoside Rg1; 1.2 Synonyms; (3α,5ξ,8α,9ξ,10α,12α,13α,14ξ,17α,20R)-3,12,25-Trihydroxy-20,24-epoxydammaran-6-yl 2-O-(6-deoxyhexopyranosyl)hexopyranoside - (3α,5ξ,8α,9ξ,10α,12α,13α,1 (3β,5ξ,6α,13α,14β)-20-(β-D-Glucopyranosyloxy)-3,12-dihydroxydammar-24-en-6-yl β-D-glucopyranoside (3β,6α,12β)-3,12-Dihydroxydammar-24-ene-6,20-diyl bis-β-D-glucopyranoside ,9ξ,10α,12α,13α,14ξ,17ξ,20ξ)-20-(hexopyranosyloxy)-3,12-dihydroxydammar-24-en-6-yl (1:1) 20-(Hexopyranosyloxy)-3,12-dihydroxydammar-24-en-6-yl hexopyranoside 4ξ,17ξ,20ξ)-20-(hexopyranosyloxy)-3,12-dihydroxydammar-24-en-6-yl hexopyranoside (1:1) Ginsenoside A2 Ginsenoside g1 Ginsenoside Rg1 mixture with ginsenoside A1 Ginsenosideg1 GinsenosideRg1 (8CI) Hexopyranoside, (3α,5ξ,8α,9ξ,10α,12α,13α,14ξ,17α,20R)-20,24-epoxy-3,12,25-trihydroxydammaran-6-yl 2-O-(6-deoxyhexopyranosyl)-, compd. with hexopyranoside, (3α,5ξ,8α Hexopyranoside, 20-(hexopyranosyloxy)-3,12-dihydroxydammar-24-en-6-yl Panaxoside A Panaxoside A (7CI) Panaxoside Rg1 Panaxsaponin Rg1 Rg1 ginsenoside Sanchinoside C1 Sanchinoside Rg1 β-D-Glucopyranoside, (3β,5ξ,6α,13α,14β)-20-(β-D-glucopyranosyloxy)-3,12-dihydroxydammar-24-en-6-yl β-D-Glucopyranoside, (3β,6α,12β)-3,12-dihydroxydammar-24-ene-6,20-diyl bis-; View all

1.3 CAS No.: 22427-39-0

1.4 CID: 441923

1.5 EINECS(EC#): 244-989-9

1.6 Molecular Formula: C42H72O14 (isomer)

1.7 Inchi: InChI=1S/C42H72O14/c1-20(2)10-9-13-42(8,56-37-34(52)32(50)30(48)25(19-44)55-37)21-11-15-40(6)28(21)22(45)16-26-39(5)14-12-27(46)38(3,4)35(39)23(17-41(26,40)7)53-36-33(51)31(49)29(47)24(18-43)54-36/h10,21-37,43-52H,9,11-19H2,1-8H3/t21-,22+,23-,24+,25+,26+,27-,28-,29+,30+,31-,32-,33+,34+,35-,36+,37-,39+,40+,41+,42-/m0/s1

1.8 InChIkey: YURJSTAIMNSZAE-HHNZYBFYSA-N

1.9 Canonical Smiles: CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CC(C4C3(CCC(C4(C)C)O)C)OC5C(C(C(C(O5)CO)O)O)O)C)O)C)OC6C(C(C(C(O6)CO)O)O)O)C

1.10 Isomers Smiles: CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(C[C@@H]([C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C

2. Properties

2.1 Density: 1.33 g/cm3

2.1 Melting point: 194～197℃

2.1 Boiling point: 898.5ºC at 760 mmHg

2.1 Refractive index: 1.601

2.1 Flash Point: 497.2ºC

2.1 Precise Quality: 800.49200

2.1 PSA: 239.22000

2.1 logP: 1.11980

2.1 Appearance: White Crystalline Powder

2.2 Storage

2.3 Chemical Properties: White solid

2.4 Color/Form: Powder

2.5 pKa: 12.91±0.70(Predicted)

2.6 StorageTemp: -20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A ginsenoside found in Panax ginseng and Panax japonicus var. major that is dammarane which is substituted by hydroxy groups at the 3beta, 6alpha, 12beta and 20 <ital pro-S positions, in which the hydroxy groups at positions 6 and 20 have been converted to the corresponding beta-D-glucopyranosides, and in which a double bond has been introduced at the 24-25 posit on. Ginsenoside Rg1Supplier

3.2 Produe Method

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: R22

4.1 Safety Statements: S2; S45

4.1 Hazard Declaration: H302

4.1 RIDADR: UN 1230 3/PG 2

4.1 Caution Statement: P301 + P312 + P330

4.1 WGK Germany: 3

4.1 RTECS: LY9537200

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

22427-39-0Total: 3 Synthesis Route

52286-59-6 108 Suppliers

22427-39-0 148 Suppliers

Literatures:
EP2570132 A2, ; Paragraph 0049; 0050; 0051 ;
Yield: null

52286-59-6 108 Suppliers

6014-42-2 15 Suppliers

22427-39-0 148 Suppliers

Literatures:
Planta Medica, , vol. 69, # 3 p. 285 - 286
Yield: null

163403-91-6

22427-39-0 148 Suppliers

Literatures:
Zou, Kun; Zhu, Shu; Tohda, Chihiro; Cai, Shaoqing; Komatsu, Katsuko Journal of Natural Products, 2002 , vol. 65, # 3 p. 346 - 351
Yield: null

7. Precursor and Product

precursor:

52286-59-6

163403-91-6

product :

492-61-5

80952-71-2

53963-43-2

8. Other Information

8.0 Mesh: A class of drugs producing both physiological and psychological effects through a variety of mechanisms. They can be divided into "specific" agents, e.g., affecting an identifiable molecular mechanism unique to target cells bearing receptors for that agent, and "nonspecific" agents, those producing effects on different target cells and acting by diverse molecular mechanisms. Those with nonspecific mechanisms are generally further classed according to whether they produce behavioral depression or stimulation. Those with specific mechanisms are classed by locus of action or specific therapeutic use. (From Gilman AG, et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p252) (See all compounds classified as Central Nervous System Agents.)

8.1 Metabolism: M1 (20- O -β- D -glucopyranosyl-20( S )- protopanaxadiol ) is a ppd-type monoglucoside ginsenoside metabolized by intestinal bacteria in humans

8.2 Mesh Entry Terms: ginsenoside Rg1

8.3 Chemical Properties: White solid

8.4 Definition: ChEBI: A ginsenoside found in Panax ginseng and Panax japonicus var. major that is dammarane which is substituted by hydroxy groups at the 3beta, 6alpha, 12beta and 20

9. Computational chemical data

Molecular Weight: 801.01300g/mol
Molecular Formula: C₄₂H₇₂O₁₄
Compound Is Canonicalized: True
XLogP3-AA: 2.7
Exact Mass: 800.49220697
Monoisotopic Mass: 800.49220697
Complexity: 1410
Rotatable Bond Count: 10
Hydrogen Bond Donor Count: 10
Hydrogen Bond Acceptor Count: 14
Topological Polar Surface Area: 239
Heavy Atom Count: 56
Defined Atom Stereocenter Count: 21
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB8PAAAAAAAAAAAAAAAAAAAAYAAAAA0aMECAAAAAGDAAAAAGgAACAAAD1SwgAMCCAAABgCAAiBCAAAAAAAgAAAACAAAAAgREAIAAQAiQAAFgAAPAAPA4PwPgAAAAAAAAADAAAYAADAAAQAACAAAAA==

10. Question & Answer

What are the pharmacological activities and preparation methods of Ginsenoside Rg1? May 21 2023
Ginsenoside Rg1, mainly derived from the roots, stems, leaves, and flower buds of plants in the Panax genus of the Araliaceae family, such as Panax ginseng, Panax notoginseng, Panax quinquefolius, Vie..

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