hernandulcin

For research use only. Not for therapeutic Use.

  • CAT Number: M006055
  • CAS Number: 95602-94-1
  • Molecular Formula: C15H24O2
  • Molecular Weight: 236.355
  • Purity: ≥95%
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<span style="color:#000000;"><span style="font-family:arial,helvetica,sans-serif;"><span style="font-size:12px;">hernandulcin (CAS&nbsp;95602-94-1),<span style="font-variant-ligatures: normal; orphans: 2; widows: 2;">a C15 sesquiterpene ketone, is a natural sweetener isolated from the leaves of Lippia dulcis. It is a promising sugar substitute due to its safety and low caloric potential.</span></span></span></span></p>


Catalog Number M006055
CAS Number 95602-94-1
Synonyms

hernandulcin;(4S)-1-Methyl-4α-[(S)-1-hydroxy-1,5-dimethyl-4-hexenyl]cyclohexene-3-one;(S)-3-Methyl-6β-[(S)-1-hydroxy-1,5-dimethyl-4-hexenyl]-2-cyclohexene-1-one;(S)-6β-[(S)-1-Hydroxy-1,5-dimethyl-4-hexenyl]-3-methyl-2-cyclohexen-1-one

Molecular Formula C15H24O2
Purity ≥95%
Storage -20°C
IUPAC Name (6S)-6-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-3-methylcyclohex-2-en-1-one
InChI InChI=1S/C15H24O2/c1-11(2)6-5-9-15(4,17)13-8-7-12(3)10-14(13)16/h6,10,13,17H,5,7-9H2,1-4H3/t13-,15+/m1/s1
InChIKey HYQNKKAJVPMBDR-HIFRSBDPSA-N
SMILES CC1=CC(=O)C(CC1)C(C)(CCC=C(C)C)O
Reference

1. Science. 1985 Jan 25;227(4685):417-9. doi: 10.1126/science.3880922.Hernandulcin: an intensely sweet compound discovered by review of ancient literature.Compadre CM, Pezzuto JM, Kinghorn AD, Kamath SK.
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Ancient Mexican botanical literature was systematically searched for new plant sources of intensely sweet substances. Lippia dulcis Trev., a sweet plant, emerged as a candidate for fractionation studies, and hernandulcin, a sesquiterpene, was isolated and judged by a human taste panel as more than 1000 times sweeter than sucrose. The structure of the sesquiterpene was determined spectroscopically and confirmed by chemical synthesis. Hernandulcin was nontoxic when administered orally to mice, and it did not induce bacterial mutation.</div>
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2.Plant Cell Rep. 1991 Apr;9(12):663-6. doi: 10.1007/BF00235352.Lippia dulcis shoot cultures as a source of the sweet sesquiterpene hernandulcin.Sauerwein M(1), Flores HE, Yamazaki T, Shimomura K.</div>
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The axenic shoot culture of Lippia dulcis Trev., Verbenaceae, was established on hormone-free Murashige-Skoog solid medium containing 3% sucrose. Shoots were cultured in various liquid or solid media. Woody Plant liquid medium was best for shoot multiplication, but the production of hernandulcin was relatively low. The highest hernandulcin content (2.9% dry wt) was obtained after 28 days of culture on Murashige-Skoog solid medium containing 2% sucrose. The addition of chitosan to the culture media enhanced the growth of shoots as well as the production of hernandulcin, especially with the liquid medium.</div>
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3. Plant Cell Rep. 1991 Feb;9(10):579-81. doi: 10.1007/BF00232336.Hernandulcin in hairy root cultures of Lippia dulcis.Sauerwein M(1), Yamazaki T, Shimomura K.</div>
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The hairy root culture of Lippia dulcis Trev., Verbenaceae, was established by transformation with Agrobacterium rhizogenes A4. The transformed roots grew well in Murashige and Skoog medium containing 2% sucrose. The roots turned light green when they were cultured under 16 h/day light. The green hairy roots produced the sweet sesquiterpene hernandulcin (ca. 0.25 mg/g dry wt) together with 20 other mono- and sesquiterpenes, while no terpenes were detected in the nontransformed root cultures. The growth and hernandulcin production in the hairy root cultures were influenced by the addition of auxins to the medium. The addition of a low concentration of chitosan (0.2 – 10.0 mg / l) enhanced the&nbsp;</div>
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production of hernandulcin 5-fold.</div>

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