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Cas Database

27013-91-8

27013-91-8

Identification

  • Product Name:alpha-Hederin

  • CAS Number: 27013-91-8

  • EINECS:248-166-5

  • Molecular Weight:750.968

  • Molecular Formula: C41H66 O12

  • HS Code:29389090

  • Mol File:27013-91-8.mol

Synonyms:(+)-Dipsacobioside;Akebia saponin PD;Akeboside Stc;Cephalaroside C;Dipsacobioside;Glycoside L-E1;Hederoside C;Helixin;Kalopanaxsaponin A;Kizuta saponin K6;Koronaroside A;NSC 106553;Nepalin 2;Prosapogenin CP3b;Pulsatilla saponin A;Sapindoside A;Tauroside E;α-Hederin;

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Safety information and MSDS view more

  • Pictogram(s):Low toxicity by ingestion.

  • Hazard Codes:Low toxicity by ingestion.

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowed

  • 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:Usbiological
  • Product Description:Alpha-Hederin
  • Packaging:20mg
  • Price:$ 433
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:α-Hederin
  • Packaging:25 mg
  • Price:$ 140
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:α-Hederin phyproof?ReferenceSubstance
  • Packaging:20 mg
  • Price:$ 412
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:α-Hederin primary pharmaceutical reference standard
  • Packaging:10mg
  • Price:$ 578
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:α-Hederin analytical standard
  • Packaging:10mg
  • Price:$ 578
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:α-Hederin
  • Packaging:5 mg
  • Price:$ 650
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  • Manufacture/Brand:DC Chemicals
  • Product Description:alpha-Hederin >98%
  • Packaging:100 mg
  • Price:$ 300
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  • Manufacture/Brand:Crysdot
  • Product Description:alpha-Hederin 98+%
  • Packaging:10mg
  • Price:$ 216
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  • Manufacture/Brand:ChemScene
  • Product Description:alpha-Hederin ≥98.0%
  • Packaging:5mg
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  • Manufacture/Brand:Chemenu
  • Product Description:alpha-Hederin 98%
  • Packaging:10mg
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Relevant articles and documentsAll total 17 Articles be found

Antifungal activity of modified hederagenin glycosides from the leaves of Kalopanax pictum var. chinense

Lee, Min-Won,Kim, Sung Uk,Hahn, Dug-Ryoung

, p. 718 - 719 (2001)

Monodesmosides which were obtained from the partial degradation of hederagenin bisdesmosides exhibited significant antifungal effect against Microsporum canis, Coccidioides immitis, Trichophyton mentagrophytes, Cryptococcus neoformans, and Candida albican

Structure of dipsacobioside

Akimaliev,Isaev,Abubakirov

, p. 202 - 203 (2002)

-

Krokhmalyuk et al.

, (1975)

Mukhamedziev et al.

, (1971)

Triterpene glycosides of Dipsacus azureus

Putieva,Mukhamedziev

, p. 341 - 342 (1998)

-

Antimicrobially active hederagenin glycosides from Cephalaria elmaliensis

Sarkahya, Nazlboeke,Krmzguel, Sueheyla

, p. 828 - 833 (2012)

A phytochemical investigation of the aerial parts of Cephalaria elmaliensis resulted in the isolation of ten hederagenin-type triterpene saponins (1-10) including three new ones, elmalienoside A (1), elmalienoside B (2), elmalienoside C (3), and two known flavonoid glycosides (11-12). Their structures were identified by extensive spectroscopic techniques (1D and 2D NMR, HR ESIMS) and chemical evidence. The antimicrobial activity of the extracts and the pure compounds was evaluated by the MIC method. According to the results, all pure compounds including the new ones were found to be very active against both gram-positive and gram-negative bacteria. Georg Thieme Verlag KG Stuttgart · New York.

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.

Triterpene glycosides from Kalopanax septemlobum. 1. Glycosides A, B, C, F, G1, G2, I2, H, and J from leaves of Kalopanax septemlobum var. maximowichii introduced to Crimea

Grishkovets,Panov,Kachala,Shashkov

, p. 194 - 199 (2008/02/01)

Eight known glycosides of hederagenin and the new triterpene glycoside 3-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2) -O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4) -O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin were isolated by chromatographic methods from leaves of Kalopanax septemlobum var. maximowichii introduced to Crimea. The known 3-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4) -O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin was observed for the first time in Kalopanax septemlobum. 2005 Springer Science + Business Media, Inc.

Synthesis of α-hederin, δ-hederin, and related triterpenoid saponins

Ple, Karen,Chwalek, Martin,Voutquenne-Nazabadioko, Laurence

, p. 1588 - 1603 (2007/10/03)

The synthesis of α-hederin (3-O-[α-L-rhamnopyranosyl-(1→2) -α-L-arabinopyranosyl]hederagenin, 1), δ-hederin (3-O-(α-L-arabinopyranosyl)hederagenin, 3), and three related triterpenoid saponins is described as part of a study of the structure-activity relationships between triterpenoid saponins and hemolytic activity. 4-Methoxybenzyl α-L-arabinopyranoside (11) was synthesized first and then used to prepare the different arabinose acceptors. Glycosylation between the acceptors and 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate (20) was performed in excellent yield to give the desired disaccharides. Coupling of the trichloroacetimidate derivatives of the disaccharides to allyl- or methyl-hederagenin gave the protected saponosides in high yields. The saponins and their corresponding methyl esters were then obtained in good to moderate yields after deprotection. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Metabolism of kalopanaxsaponin K by human intestinal bacteria and antirheumatoid arthritis activity of their metabolites.

Kim, Dong-Hyun,Bae, Eun-Ah,Han, Myung Joo,Park, Hee-Juhn,Choi, Jong-Won

, p. 68 - 71 (2007/10/03)

When kalopanaxsaponin K (KPK) from Kalopanax pictus was incubated for 24 h at 37 degrees C with human intestinal microflora, KPK was mainly metabolized to kalopanaxsaponin I (KPI) via kalopanaxsaponin H (KPH) rather than via kalopanaxsaponin J (KPJ), and then transformed to kalopanaxsaponin A (KPA) and hederagenin. Bacteroides sp., and Bifidobacterium sp. and Fusobacterium sp. transformed KPK to KPI and KPA and hederagenin via KPH or KPJ. However, Lactobacillus sp. and Streptococcus sp. transformed KPK to KPI, KPA, and hederagenin only via KPJ. The metabolite KPA of KPK showed potent antirheumatoid arthritis activity.

Process route upstream and downstream products

Process route

hederagenin-3-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester
119742-55-1

hederagenin-3-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester

hedaragenin
465-99-6

hedaragenin

prosapogenin
17184-21-3

prosapogenin

alpha-Hederin
27013-91-8

alpha-Hederin

Conditions
Conditions Yield
With Bacteroides JY-6; Bifidobacterium K-111; In various solvent(s); at 37 ℃; for 36h;
35 mg
6 mg
17 mg
5 mg
prosapogenin
17184-21-3

prosapogenin

hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester
99624-66-5

hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester

alpha-Hederin
27013-91-8

alpha-Hederin

Conditions
Conditions Yield
With sulfuric acid; In ethanol; for 2h; Further byproducts given; Heating;
135 mg
270 mg
prosapogenin
17184-21-3

prosapogenin

3-O-<α-L-arabinopyranosyl>hederagenin 28-O-<β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside>
39524-08-8

3-O-<α-L-arabinopyranosyl>hederagenin 28-O-<β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside>

hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester
99624-66-5

hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester

alpha-Hederin
27013-91-8

alpha-Hederin

Conditions
Conditions Yield
With sulfuric acid; In ethanol; for 2h; Further byproducts given; Heating;
135 mg
180 mg
prosapogenin
17184-21-3

prosapogenin

hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester
99624-66-5

hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester

3β,23-dihydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl ester
57539-70-5

3β,23-dihydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl ester

alpha-Hederin
27013-91-8

alpha-Hederin

Conditions
Conditions Yield
With sulfuric acid; In ethanol; for 2h; Further byproducts given; Heating;
135 mg
155 mg
prosapogenin
17184-21-3

prosapogenin

hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester
99624-66-5

hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester

cauloside D
12672-45-6

cauloside D

alpha-Hederin
27013-91-8

alpha-Hederin

Conditions
Conditions Yield
With sulfuric acid; In ethanol; for 2h; Further byproducts given; Heating;
135 mg
hederagenin 3-O-β-D-glucopyranosyl-(1->4)-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside
904684-90-8

hederagenin 3-O-β-D-glucopyranosyl-(1->4)-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside

hedaragenin
465-99-6

hedaragenin

alpha-Hederin
27013-91-8

alpha-Hederin

Conditions
Conditions Yield
With Bifidobacterium K103; general anaerobic medium; at 37 ℃; for 20h; Further Variations:; Reagents; Product distribution;
0.00686 mmol
0.00242 mmol
0.00446 mmol
3-O-β-D-glucopyranosyl (1-4)-β-D-xylopyranosyl (1-3)-α-L-rhamnopyranosyl (1-2)-α-L-arabinopyranosyl-23-hydroxyolean-12-en-28-O-α-L-rhamnopyranosyl (1-4)-β-D-glucopyranosyl (1-6)-β-D-glucopyranosyl ester

3-O-β-D-glucopyranosyl (1-4)-β-D-xylopyranosyl (1-3)-α-L-rhamnopyranosyl (1-2)-α-L-arabinopyranosyl-23-hydroxyolean-12-en-28-O-α-L-rhamnopyranosyl (1-4)-β-D-glucopyranosyl (1-6)-β-D-glucopyranosyl ester

hederagenin-3-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester
119742-55-1

hederagenin-3-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester

alpha-Hederin
27013-91-8

alpha-Hederin

hederagenin 3-O-β-D-glucopyranosyl-(1->4)-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside
904684-90-8

hederagenin 3-O-β-D-glucopyranosyl-(1->4)-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside

Conditions
Conditions Yield
With Eubacterium A44; general anaerobic medium; at 37 ℃; for 20h; Further Variations:; Reagents; Product distribution;
0.00415 mmol
0.00279 mmol
0.00428 mmol
0.00099 mmol
alpha-Hederin
27013-91-8

alpha-Hederin

Conditions
Conditions Yield
With potassium hydroxide; water; for 1h; Heating;
40 mg
With potassium hydroxide; In methanol; water; at 100 ℃; for 2h;
With ammonium hydroxide; In ethanol; for 15h; Reflux;
hederagenin-3-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-6-O-acetyl-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester
97240-03-4

hederagenin-3-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-6-O-acetyl-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester

alpha-Hederin
27013-91-8

alpha-Hederin

Conditions
Conditions Yield
With potassium hydroxide; for 0.5h; Heating;
6 mg
Multi-step reaction with 2 steps
1: ammonia / ethanol; H2O / 20 °C
2: KOH / H2O; methanol / 2 h / 100 °C
With potassium hydroxide; ammonia; In methanol; ethanol; water;
Multi-step reaction with 2 steps
1: 14 mg / 0.1 N aq. KOH / 20 h / Ambient temperature
2: 0.05 N H2SO4 / ethanol / 2 h / Heating
With potassium hydroxide; sulfuric acid; In ethanol;
Multi-step reaction with 2 steps
1: 14 mg / 0.1 N aq. KOH / 20 h / Ambient temperature
2: 0.05 N H2SO4 / ethanol / 2 h / Heating
With potassium hydroxide; sulfuric acid; In ethanol;
Multi-step reaction with 2 steps
1: 14 mg / 0.1 N aq. KOH / 20 h / Ambient temperature
2: 0.05 N H2SO4 / ethanol / 2 h / Heating
With potassium hydroxide; sulfuric acid; In ethanol;
Multi-step reaction with 2 steps
1: 14 mg / 0.1 N aq. KOH / 20 h / Ambient temperature
2: 0.05 N H2SO4 / ethanol / 2 h / Heating
With potassium hydroxide; sulfuric acid; In ethanol;
3-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl hederagenin-28-O-β-D-galactopyranosyl-(1->6)-β-D-glucopyranosyl ester
942997-00-4

3-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl hederagenin-28-O-β-D-galactopyranosyl-(1->6)-β-D-glucopyranosyl ester

alpha-Hederin
27013-91-8

alpha-Hederin

Conditions
Conditions Yield
3-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl hederagenin-28-O-β-D-galactopyranosyl-(1->6)-β-D-glucopyranosyl ester; With potassium hydroxide; In water; at 80 ℃; for 2h;
With hydrogenchloride; In water;

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