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    Limonin

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      Limonin

      SKU
      L0280

      Category: Phytochemicals

      Synonyms
      7,16-Dioxo-7,16-dideoxylimondiol , Limonoic acid di-δ-lactone , Citrolimonin , Dictamnolactone , Evodin , Limonine , Obaculactone , NSC 36508
      1180-71-8
      CAS-Number
      C26H30O8
      Molecular Formula
      470.51
      Molecular Weight

      For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

      • Product Data
      • Handling
      • Safety Information
      • Details

      Specifications

      Purity
      ≥98% (HPLC)
      Appearance
      White to off-white powder
      Identity
      1H-NMR

      Properties

      Solvents
      DMSO (10mg/ml), DMF (20mg/ml)

      Documentation

      Safety Data Sheet (SDS)
      CDX L0280 MSDS.pdf
      Shipping
      AMBIENT
      Short Term Storage
      +4°C
      Long Term Storage
      -20°C
      Handling Advice
      Protect from light and moisture.
      Use / Stability
      Stable for at least 2 years after receipt when stored at -20°C.
      Transportation
      Not dangerous goods
      Description
      Limonin is the first described limonoid, which are naturally occurring tetranortriterpenoids that impart bitter flavor in citrus fruits. Compounds belonging to this group have reported anti-proliferative and proapoptotic activity on several cancer cell lines as well as pesticidal, anti-malarial, anti-microbial, anti-HIV, anti-inflammatory, antinociceptive and neuroprotective activity. Shown to inhibit arginase I and II and P-glycoprotein. May be used in assays as control, standard or competitor, or in studies on the physiology, metabolism and biosynthesis of limonin.
      Smiles
      O=C1[C@@]2(C)[C@@]34O[C@@H]3C(O[C@@H](C5=COC=C5)[C@]4(C)CC[C@]2([H])[C@]67[C@](C1)([H])C(C)(C)O[C@@]6([H])CC(OC7)=O)=O
      InChi Key
      KBDSLGBFQAGHBE-MSGMIQHVSA-N
      References
      (1) V.P. Maier, et al., ACS Symposium Series 143, 63 (1980) , (2) J.A. Klocke & I. Kubo, Ent. Exp. & Appl. 32, 299 (1982) , (3) H. Matsuda, et al., Planta Med. 64, 339 (1998) , (4) L. Battinelli, et al., Planta Med. 69, 910 (2003) , (5) A. Roy & S. Saraf, Biol. Pharm. Bull. 29, 191 (2006) (Review) , (6) J.S. Yoon, et al., J. Nat. Prod. 71, 208 (2008) , (7) J.S. Yoon, et al., Mol. Neurosci. 42, 9 (2010) , (8) M.Z. El-Readi, et al., Eur. J. Pharmacol. 626, 139 (2010) , (9) K.N. Chidambara Murthy, et al., J. Agric. Food Chem. 59, 2314 (2011) , (10) A. Rahman, et al., Anticancer Agents Med. Chem. 15, 236 (2015) , (11) R. Gualdani, et al., Molecules 21, E1530 (2016) (Review) , (12) B.H. Koo, et al., Yonsei Med. J. 59, 366 (2018)
      InChi
      InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1

      Limonin is the first described limonoid, which are naturally occurring tetranortriterpenoids that impart bitter flavor in citrus fruits. Compounds belonging to this group have reported anti-proliferative and proapoptotic activity on several cancer cell lines as well as pesticidal, anti-malarial, anti-microbial, anti-HIV, anti-inflammatory, antinociceptive and neuroprotective activity. Shown to inhibit arginase I and II and P-glycoprotein. May be used in assays as control, standard or competitor, or in studies on the physiology, metabolism and biosynthesis of limonin.

      SKU: L0280 Category: Phytochemicals
      • Additional information

      Additional information

      Synonyms

      7,16-Dioxo-7,16-dideoxylimondiol, Limonoic acid di-δ-lactone, Citrolimonin, Dictamnolactone, Evodin, Limonine, Obaculactone, NSC 36508

      Purity

      ≥98% (HPLC)

      Appearance

      White to off-white powder

      CAS-Number

      1180-71-8

      Molecular Formula

      C26H30O8

      Molecular Weight

      470.51

      Identity

      1H-NMR

      Solvents

      DMSO (10mg/ml), DMF (20mg/ml)

      Smiles

      O=C1[C@@]2(C)[C@@]34O[C@@H]3C(O[C@@H](C5=COC=C5)[C@]4(C)CC[C@]2([H])[C@]67[C@](C1)([H])C(C)(C)O[C@@]6([H])CC(OC7)=O)=O

      InChi Key

      KBDSLGBFQAGHBE-MSGMIQHVSA-N

      Shipping

      AMBIENT

      Short Term Storage

      +4°C

      Long Term Storage

      -20°C

      Handling Advice

      Protect from light and moisture.

      Use / Stability

      Stable for at least 2 years after receipt when stored at -20°C.

      Transportation

      Not dangerous goods

      References

      (1) V.P. Maier, et al., ACS Symposium Series 143, 63 (1980), (2) J.A. Klocke & I. Kubo, Ent. Exp. & Appl. 32, 299 (1982), (3) H. Matsuda, et al., Planta Med. 64, 339 (1998), (4) L. Battinelli, et al., Planta Med. 69, 910 (2003), (5) A. Roy & S. Saraf, Biol. Pharm. Bull. 29, 191 (2006) (Review), (6) J.S. Yoon, et al., J. Nat. Prod. 71, 208 (2008), (7) J.S. Yoon, et al., Mol. Neurosci. 42, 9 (2010), (8) M.Z. El-Readi, et al., Eur. J. Pharmacol. 626, 139 (2010), (9) K.N. Chidambara Murthy, et al., J. Agric. Food Chem. 59, 2314 (2011), (10) A. Rahman, et al., Anticancer Agents Med. Chem. 15, 236 (2015), (11) R. Gualdani, et al., Molecules 21, E1530 (2016) (Review), (12) B.H. Koo, et al., Yonsei Med. J. 59, 366 (2018)

      InChi

      InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1

      Quantity

      50 mg, Bulk

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