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

Product Data
Handling
Safety Information
Details

Specifications

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

Properties

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

Downloads

Safety Data Sheet: CDX L0280 MSDS.pdf

Short Term Storage: +4°C
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.
Handling Advice: Protect from light and moisture.
Long Term Storage: -20°C
Shipping: AMBIENT

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.
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
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 Key: KBDSLGBFQAGHBE-MSGMIQHVSA-N
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

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