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A9855

Sigma-Aldrich

3-Acetyl-11-keto-BETA-boswellic acid

from Boswellia serrata

Synonyme(s) :

AKBA

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About This Item

Formule empirique (notation de Hill) :
C32H48O5
Numéro CAS:
67416-61-9
Poids moléculaire :
512.72
Numéro MDL:
MFCD03788777
Code UNSPSC :
12352106
Nomenclature NACRES :
NA.25
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Source biologique

Boswellia serrata

Forme

powder

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

−20°C

Chaîne SMILES 

O([C@H]1[C@]([C@H]2[C@@]([C@@H]3[C@]([C@@]4(CC[C@@]5([C@@H]([C@H]([C@@H](CC5)C)C)C4=CC3=O)C)C)(CC2)C)(CC1)C)(C)C(=O)O)C(=O)C

InChI

1S/C32H48O5/c1-18-9-12-28(4)15-16-30(6)21(25(28)19(18)2)17-22(34)26-29(5)13-11-24(37-20(3)33)32(8,27(35)36)23(29)10-14-31(26,30)7/h17-19,23-26H,9-16H2,1-8H3,(H,35,36)/t18-,19+,23-,24-,25+,26-,28-,29+,30-,31-,32-/m1/s1

Clé InChI

HMMGKOVEOFBCAU-BCDBGHSCSA-N

Catégories apparentées

Description générale

Acetyl-11-keto-β-boswellic acid (AKBA) is extracted from the resin of Boswellia serrata.[1]

Application

3-Acetyl-11-keto-β-boswellic acid (AKBA) has been used:
  • to test its effects as an anti-proliferating agent on hepatic stellate cells (HSCs) proliferation and synergism in combination with imatinib in in vitro models[2]
  • to study its anti-osteoporotic activity on ovariectomy-induced osteoporosis in female Sprague Dawley rats[3]
  • in a comparative study with aspirin to test its effects as an anti-inflammatory drug to prevent intestinal adenomatous polyposis in APCMin/+ mice[4]

Actions biochimiques/physiologiques

Acetyl-11-keto-β-boswellic acid (AKBA) displays antibacterial and anti-biofilm activities against Staphylococcus epidermidis and S. aureus, respectively.[5] It is an activator of nuclear factor erythroid-2-related factor 2 (Nrf2) and exerts neuroprotective properties against ischemic injury in both in vitro and in vivo studies.[1]
Acetyl-11-keto-beta-boswellic acid is a pentacyclic triterpene that inhibits 5-lipoxygenase in a selective, enzyme-directed, nonredox, and noncompetitive manner. It has also been shown to inhibit topoisomerase I and NF-κB signaling.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000441221
0000441221
0000407710
0000407710
0000404077

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Alsaba F Raja et al.
BMC microbiology, 11, 54-54 (2011-03-17)
Boswellic acids are pentacyclic triterpenes, which are produced in plants belonging to the genus Boswellia. Boswellic acids appear in the resin exudates of the plant and it makes up 25-35% of the resin. β-boswellic acid, 11-keto-β-boswellic acid and acetyl-11-keto-β-boswellic acid
Yi Ding et al.
Scientific reports, 4, 7002-7002 (2014-11-12)
Stroke is a complex disease involved oxidative stress-related pathways in its pathogenesis. The nuclear factor erythroid-2-related factor 2 (Nrf2)/heme oxygenase-1 (HO-1) pathway has been considered a potential target for neuroprotection in stroke. Acetyl-11-Keto-β-Boswellic Acid (AKBA) is an active triterpenoid compound
Bandar E Al-Dhubiab et al.
Nutrients, 12(10) (2020-10-22)
Estrogen is instrumental in the pathological process of osteoporosis because a deficiency of this hormone increases the release of bone-resorbing cytokines. Acetyl-11-keto-β-boswellic acid (AKBA), a constituent from Boswellia serrata, has an anti-inflammatory effect by inhibiting tumor necrosis factor-α (TNF-α) expression
Ruiqi Wang et al.
Drug discoveries & therapeutics, 8(1), 25-32 (2014-03-22)
Acetyl-11-keto-beta-BA (AKBA), a component of the gum resin of Boswellia serrata, has been recognized as a promising agent for the prevention of intestinal tumorigenesis. Aspirin, a non-steroidal anti-inflammatory drug (NSAID), has also been considered to have the activity against intestinal
Mona Abdel-Tawab et al.
Clinical pharmacokinetics, 50(6), 349-369 (2011-05-11)
Non-steroidal anti-inflammatory drug (NSAID) intake is associated with high prevalence of gastrointestinal or cardiovascular adverse effects. All efforts to develop NSAIDs that spare the gastrointestinal tract and the cardiovasculature are still far from achieving a breakthrough. In the last two
Afficher tous les articles scientifiques apparentés

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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