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Cas Database

17184-21-3

17184-21-3

Identification

  • Product Name:Olean-12-en-28-oicacid, 3-(a-L-arabinopyranosyloxy)-23-hydroxy-,(3b,4a)-

  • CAS Number: 17184-21-3

  • EINECS:

  • Molecular Weight:604.825

  • Molecular Formula: C35H56 O8

  • HS Code:

  • Mol File:17184-21-3.mol

Synonyms:LeontosideA (8CI); 3-O-[a-L-Arabinopyranosyl]hederagenin;3b-(a-L-Arabinopyranosyloxy)-23-hydroxyolean-12-en-28-oicacid; Akebia saponin PA; Akeboside Stb; Cauloside A; Fatsiaside B1; GlycosideL-B2; Hederagenin 3-O-a-L-arabinopyranoside; Hederoside A3; Kizuta saponin K3; Nepalin 1;Polypetaloside B; Prosapogenin CP1; Saponin K3; Scabioside A; Scabioside A(Patrinia); Tauroside B; b2-Fatsin; d-Hederin

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:Crysdot
  • Product Description:CaulosideA 95+%
  • Packaging:5mg
  • Price:$ 723
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  • Manufacture/Brand:ChemScene
  • Product Description:CaulosideA
  • Packaging:1mg
  • Price:$ 200
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  • Manufacture/Brand:ChemScene
  • Product Description:CaulosideA
  • Packaging:5mg
  • Price:$ 500
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  • Manufacture/Brand:Arctom
  • Product Description:CaulosideA ≥98%
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Relevant articles and documentsAll total 27 Articles be found

A TRITERPENOID SAPONIN FROM FICARIA RANUNCULOIDES TUBERS

Texier, O.,Ahond, A.,Regerat, F.,Pourrat, H.

, p. 2903 - 2906 (1984)

One of the minor saponins extracted from the tubers of Ficaria ranunculoides and purified by fermentation may be 3-O-(α-arabinopyranosyl-1')28-O-6''(α-rhamnopyranosyl-1'''->4'')β-glucopyranosyl-1''>-hederagenin.On the basis of chemical degradation and spectral analysis, the structure of this new saponin is proposed. Key Word Index - Ficaria ranunculoides; Ranunculaceae; triterpenoid saponin; 3-O-(α-arabinopyranosyl-1')28-O-6''(α-rhamnopyranosyl-1'''->4'')β-glucopyranosyl 1''>-hederagenin.

Cytotoxic and immunomodulator potential of hederagenin saponins from Cephalaria tchihatchewii

Sarikahya, Nazli Boke,Mkouboi, Mohamed Chanfiou,Nalbantsoy, Ayse,Elibol, Murat

, p. 216 - 221 (2021)

Two newly described oleanane-type saponins (1–2), named tchihatchewosides A–B, along with thirteen known compounds, were isolated from the aerial parts of Cephalaria tchihatchewii using several type of chromatography processes. The structures of all compounds (1-15) were determined by spectroscopic (1D- and 2D-NMR, HR-ESI/MS) and chemical methods. The cytotoxic activities on CCD 34Lu, A549, CRL5807, CRL 5826, HTB-177 and HeLa cell lines of newly described compounds 1–2 and 1a-2a were evaluated by MTT method using doxorubicin as positive control. Immunomodulatory activity was performed with PMA plus ionomycin in stimulated whole blood cells treated with saponins. The supernatant was analyzed for IL-4, IFN-γ and IL1β cytokines by ELISA. DMSO was considered as the negative control. The results showed that the only compound 1a was exhibited moderate cytotoxicity against CRL 5826 and CCD 34Lu cells. The compounds 1–2 and prosapogenins 1a-2a stimulated IL1β cytokine release, indicating that they might potentially stimulate the innate immune response.

Antibacterial activity of a triterpenoid saponin from the stems of Caesalpinia pulcherrima Linn.

Asati, Nidhi,Yadava

, p. 499 - 507 (2017/09/30)

A new compound 1 was isolated from the methanolic extract of the stems of the Caesalpinia pulcherrima Linn. along with a reported compound (2) 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester. The new compound 1 has m.p. 272–274°C, m.f. C46H74O17, [M]+ m/z 898. It was characterised as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl hederagenin 28-O-β-D- xylopyranosyl ester by various colour reactions, chemical degradations and spectral analyses. Antibacterial activity of compound 1 was screened against various Gram-positive and Gram-negative bacteria and showed significant results.

Impact of Scaffold Exploration on Novel Dual-Acting Histone Deacetylases and Phosphodiesterase 5 Inhibitors for the Treatment of Alzheimer’s Disease

Sánchez-Arias, Juan A.,Rabal, Obdulia,Cuadrado-Tejedor, Mar,De Miguel, Irene,Pérez-González, Marta,Ugarte, Ana,Sáez, Elena,Espelosin, Maria,Ursua, Susana,Haizhong, Tan,Wei, Wu,Musheng, Xu,Garcia-Osta, Ana,Oyarzabal, Julen

, p. 638 - 661 (2017/03/20)

A novel systems therapeutics approach, involving simultaneous inhibition of phosphodiesterase 5 (PDE5) and histone deacetylase (HDAC), has been validated as a potentially novel therapeutic strategy for the treatment of Alzheimer’s disease (AD). First-in-class dual inhibitors bearing a sildenafil core have been very recently reported, and the lead molecule 7 has proven this strategy in AD animal models. Because scaffolds may play a critical role in primary activities and ADME-Tox profiling as well as on intellectual property, we have explored alternative scaffolds (vardenafil- and tadalafil-based cores) and evaluated their impact on critical parameters such as primary activities, permeability, toxicity, and in vivo (pharmacokinetics and functional response in hippocampus) to identify a potential alternative lead molecule bearing a different chemotype for in vivo testing.

Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis

Wang, Xiao-Yang,Gao, Hui,Zhang, Wei,Li, Yuan,Cheng, Guang,Sun, Xiao-Li,Tang, Hai-Feng

, p. 5714 - 5720 (2013/10/01)

Investigation of the n-BuOH extract of the rhizomes of Anemone taipaiensis led to the isolation of five new oleanane-type triterpenoid saponins (1-5), together with seven known saponins (6-12). Their structures were determined by the extensive use of 1D and 2D NMR experiments along with ESIMS analyses and acid hydrolysis. The aglycone of 1, 2 and 4 was determined as siaresinolic acid, which was reported in this genus for the first time. The cytotoxicities of the saponins 1-12, prosapogenins 4a, 5a, 10a-12a and sapogenins siaresinolic acid (SA), oleanolic acid (OA), hederagenin (HE) were evaluated against five human cancer cell lines, including HepG2, HL-60, A549, HeLa and U87MG. The monodesmosidic saponins 6-8, 5a, 10a-12a and sapogenins SA, OA, HE exhibited cytotoxic activity toward all cancer cell lines, with IC 50 values ranging from 2.25 to 57.28 μM. Remarkably, the bisdesmosidic saponins 1-4 and 9 showed selective cytotoxicity against the U87MG cells.

Drug to genome to drug: Discovery of new antiplasmodial compounds

Beghyn, Terence B.,Charton, Julie,Leroux, Florence,Laconde, Guillaume,Bourin, Arnaud,Cos, Paul,Maes, Louis,Deprez, Benoit

, p. 3222 - 3240 (2011/06/27)

Figure Presented. The dominant strategy for discovery of new antimalarial drugs relies on cell-free assays on specific biochemical pathways of Plasmodium falciparum. However, it appears that screening directly on the parasite is a more rewarding approach. The drug to genome to drug approach consists of testing a small set of structural analogues of a drug acting on human proteins that have plasmodial orthologues. Both man and plasmodium possess cyclic nucleotide phosphodiesterases (PDEs) that are key players of cell homeostasis. We synthesized and tested 40 analogues of tadalafil, a human PDE5 inhibitor, on P. falciparum in culture and obtained potent inhibitors of parasite growth. We discuss the structure-activity relationships, which support the hypothesis that our compounds kill the parasite via inhibition of plasmodial PDE activity. We also prove that antiplasmodial derivatives inhibit the hydrolysis of cyclic nucleotides of the parasite, validating the cAMP/cGMP pathways as therapeutic targets against Plasmodium falciparum.

Process route upstream and downstream products

Process route

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
171596-36-4

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions
Conditions Yield
With ammonia; In methanol; at 45 ℃; for 20h;
70%
With ammonia; In methanol; at 40 ℃; for 72h;
68%
With ammonia; In methanol; Reflux;
60%
With ammonia; Heating;
31%
(1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate
171596-41-1

(1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
171596-36-4

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 83 percent / triethylamine / CHCl3 / -10 °C
2: 70 percent / NH3 / methanol / 20 h / 45 °C
With ammonia; triethylamine; In methanol; chloroform;
Multi-step reaction with 2 steps
1: 93 percent / NaHCO3 / CHCl3 / 20 °C
2: 31 percent / methanolic NH3 / Heating
With ammonia; sodium hydrogencarbonate; In chloroform;
Multi-step reaction with 2 steps
1: triethylamine / chloroform / -10 °C
2: ammonia / methanol / Reflux
With ammonia; triethylamine; In methanol; chloroform;
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 3 h / 20 °C
2: ammonia / methanol / 72 h / 40 °C
With ammonia; triethylamine; In tetrahydrofuran; methanol;
D-Tryptophan methyl ester
4299-70-1,7303-49-3,22032-65-1

D-Tryptophan methyl ester

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
171596-36-4

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 42 percent / TFA / CH2Cl2 / 20 °C
2: 93 percent / NaHCO3 / CHCl3 / 20 °C
3: 31 percent / methanolic NH3 / Heating
With ammonia; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; chloroform; 1: Pictet-Spengler reaction;
Multi-step reaction with 3 steps
1: trifluoroacetic acid / dichloromethane / 24 h / 0 - 20 °C / Molecular sieve
2: triethylamine / chloroform / -10 °C
3: ammonia / methanol / Reflux
With ammonia; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; chloroform; 1: Pictet-Spengler cyclisation;
(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
171596-36-4

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 42 percent / TFA / CH2Cl2 / 20 °C
2: 93 percent / NaHCO3 / CHCl3 / 20 °C
3: 31 percent / methanolic NH3 / Heating
With ammonia; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; chloroform; 1: Pictet-Spengler reaction;
(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
171596-36-4

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: trifluoroacetic acid / dichloromethane / 24 h / 0 - 20 °C / Molecular sieve
2: triethylamine / chloroform / -10 °C
3: ammonia / methanol / Reflux
With ammonia; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; chloroform; 1: Pictet-Spengler cyclisation;
Multi-step reaction with 3 steps
1: isopropyl alcohol / Reflux
2: triethylamine / tetrahydrofuran / 3 h / 20 °C
3: ammonia / methanol / 72 h / 40 °C
With ammonia; triethylamine; In tetrahydrofuran; methanol; isopropyl alcohol;
piperonol
495-76-1

piperonol

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
171596-36-4

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: manganese(IV) oxide / dichloromethane / 20 °C
2: isopropyl alcohol / Reflux
3: triethylamine / tetrahydrofuran / 3 h / 20 °C
4: ammonia / methanol / 72 h / 40 °C
With manganese(IV) oxide; ammonia; triethylamine; In tetrahydrofuran; methanol; dichloromethane; isopropyl alcohol;
(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
171596-36-4

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 23 percent / trifluoroacetic acid / CH2Cl2 / 24 h / 20 °C
2: 83 percent / triethylamine / CHCl3 / -10 °C
3: 70 percent / NH3 / methanol / 20 h / 45 °C
With ammonia; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; chloroform; 1: Pictet-Spengler reaction;
(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
171596-36-4

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 23 percent / trifluoroacetic acid / CH2Cl2 / 24 h / 20 °C
2: 83 percent / triethylamine / CHCl3 / -10 °C
3: 70 percent / NH3 / methanol / 20 h / 45 °C
With ammonia; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; chloroform; 1: Pictet-Spengler reaction;
(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
171596-36-4

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions
Conditions Yield
cauloside D
12672-45-6

cauloside D

prosapogenin
17184-21-3

prosapogenin

Conditions
Conditions Yield
With potassium hydroxide; In ethanol; for 2h; Heating;
15 mg
With potassium hydroxide; In methanol; water; at 100 ℃; for 2h;
Alkaline hydrolysis;
With potassium hydroxide; In methanol; water; at 100 ℃; for 2h;
Multi-step reaction with 2 steps
1: aq. HCl / 0.07 h / Heating
2: 17 mg / KOH / ethanol / 2 h / Heating
With hydrogenchloride; potassium hydroxide; In ethanol;
With ammonium hydroxide; In ethanol; for 15h; Reflux;

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