Tephrosin

Tephrosin is an anti-cancer rotenoid isolated from the plant, Tephrosia vogelii.

Natural rotenoids display a wide range of biological activities, from strong pesticidal and insecticidal activities to therapeutically intriguing anticancer properties. Tephrosin has been shown to induce caspase-independent apoptosis, and internalization and degradation of inactivated EGFR and ErB2 in human colon cancer cells.

From the laboratory of Hannah F. Sore, PhD, University of Cambridge.

Catalog Number Product Size AVAILABILITY Price Qty
ECM001
Tephrosin
1mg 1-2 weeks
Regular Price:$199.00
Specifications

Product Type: Small Molecule
Chemical Formula: C23H22O7
Molecular Weight: 410.14
Format: Yellow Solid
Purity: >95% by 1H NMR
Solubility: Unknown
Spectral Information: Rf 0.30 (hexane-ethyl acetate; 1:1); [α]D20 -88 (c 0.1 in CHCl3); νmax (neat)/cm-1 3600-3300w br, 1674m (C=O)ketone, 1596m, 1577m, 1509m, 1441m, 1330m, 1270m, 1218m, 1200m, 1159m, 1109m, 1087m, 1027m, 884m, 816m; δH (500 MHz, CDCl3) 1.39 (3H, s, C(7’)H3), 1.45 (3H, s, C(8’)H3), 3.73 (3H, s, C(2’)H3), 3.81 (3H, s, C(3’)H3), 4.40 (1H, s, C(12a)OH), 4.49 (1H, dd, J 1.0, 12.0 Hz, C(6)HH’), 4.57 (1H, dd, J 1.0, 2.5 Hz, C(6a)H), 4.63 (1H, dd, J 2.5, 12.0 Hz, C(6)HH’), 5.55 (1H, d, J 10.0 Hz, C(5’)H), 6.47 (1H, d, J 9.0 Hz, C(10)H), 6.48 (1H, s, C(4)H), 6.56 (1H, s, C(1)H), 6.60 (1H, d, J 10.0 Hz, C(4’)H), 7.72 (1H, d, J 11.0 Hz, C(11)H); δ¬C (125 MHz, CDCl3) 28.3 (C(7’)H3), 28.5 (C(8’)H3), 55.9 (C(3’)H3), 56.3 (C(2’)H3), 63.8 (C(6)H2), 67.4 (C(12a)), 76.2 (C(6a)H), 78.0 (C(6’)), 101.0 (C(4)H), 108.6 (C(13)), 109.1 (C(8)), 109.3 (C(1)H), 111. (C(11a)), 111.9 (C(10)H), 115.4 (C(4’)H), 128.5 (C(11)H), 128.8 (C(5’)H), 143.9 (C(2)), 148.4 (C(3)), 151.1 (C(4a)), 156.6 (C(7a)), 160.8 (C(9)), 191.4 (C(12)); LRMS m/z found 393.1, C23H22O6 [M-H2O+H]+ requires 393.1; HRMS m/z found 433.1262, C23H22O7Na [M+Na]+ requires 433.1258. See also: PDF Tephrosin Spectral Information.
Storage: -20C
Shipped: Room temperature

Provider
From the laboratory of Hannah F. Sore, PhD, University of Cambridge.

References
  1. Russell DA, Freudenreich JJ, Ciardiello JJ, Sore HF, Spring DR. Stereocontrolled semi-syntheses of deguelin and tephrosin. Org Biomol Chem. 2017;15(7):1593-1596.

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