Trichotomine

Last updated
Trichotomine
Trichotomine.png
Names
IUPAC name
(2E,5S)-2-[(5S)-5-carboxy-3-oxo-6,11-dihydro-5H-indolizino[8,7-b]indol-2-ylidene]-3-oxo-6,11-dihydro-5H-indolizino[8,7-b]indole-5-carboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C30H20N4O6/c35-27-17(11-21-25-15(9-23(29(37)38)33(21)27)13-5-1-3-7-19(13)31-25)18-12-22-26-16(14-6-2-4-8-20(14)32-26)10-24(30(39)40)34(22)28(18)36/h1-8,11-12,23-24,31-32H,9-10H2,(H,37,38)(H,39,40)/b18-17+/t23-,24-/m0/s1
    Key: LOHPAPKRMNSIDN-GKIAHDCUSA-N
  • InChI=1S/C30H20N4O6/c35-27-17(11-21-25-15(9-23(29(37)38)33(21)27)13-5-1-3-7-19(13)31-25)18-12-22-26-16(14-6-2-4-8-20(14)32-26)10-24(30(39)40)34(22)28(18)36/h1-8,11-12,23-24,31,35H,9-10H2,(H,37,38)(H,39,40)/t23-,24-/m0/s1
    Key: LGVWLGJCDLVSOA-ZEQRLZLVSA-N
  • C1[C@H](N2C(=C/C(=C\3/C=C4C5=C(C[C@H](N4C3=O)C(=O)O)C6=CC=CC=C6N5)/C2=O)C7=C1C8=CC=CC=C8N7)C(=O)O
  • C1[C@H](N2C(=CC(=C2O)C3=CC4=C5C(=C6C=CC=CC6=N5)C[C@H](N4C3=O)C(=O)O)C7=C1C8=CC=CC=C8N7)C(=O)O
Properties
C30H20N4O6
Molar mass 532.512 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trichotomine is a bright blue pigment found in the berries of the plant Clerodendrum trichotomum , which is native to China and Japan. It has a novel chromophore structure which differs from previously studied plant pigments. [1] The amount of pigment in the berries increases as they become ripe. [2]

Contents

History and usage

The berries of C. trichotomum have historically been used in natural dyes. In 1978, a team of researchers at Nagoya University proposed that trichotomine was the pigment responsible for the color. [1] [3] This was confirmed in 1992. [4]

Amid growing concern about the impacts of consuming artificial food colorants, scientists have studied trichotomine as a potential plant-based alternative to produce blue food dye. It is of interest partly because blue pigment is so rare in nature, so the number of viable options for pass production are significantly more limited than a more common pigment, like red. San-Ei Gen, a Japanese colorant manufacturer, has produced an extract of the pigment and used it for testing purposes. They found that trichotomine is not acutely poisonous to mice. [3]

See also

References

  1. 1 2 Iwadare, S.; Shizuri, Y.; Yamada, K.; Hirata, Y. (1978-01-01). "Synthesis of trichotomine, a blue pigment obtained from clerodendron trichotomum thunb" . Tetrahedron. 34 (10): 1457–1459. doi:10.1016/0040-4020(78)80166-5. ISSN   0040-4020.
  2. ↑ "Clerodendrum trichotomum (Harlequin Glorybower)". Cambridge University Botanic Garden. Retrieved 2025-10-03.
  3. 1 2 Yarnell, Amanda (2025-01-21). "Bringing Blue To A Plate Near You". Chemical & Engineering News. Retrieved 2025-08-26.
  4. ↑ Koda, Takatoshi; Ichi, Takahito; Odake, Kinnosuke; Furuta, Hideo; Sekiya, Jiro (January 1992). "Blue Pigment Formation by Clerodendron trichotomum callus" . Bioscience, Biotechnology, and Biochemistry. 56 (12): 2020–2022. doi:10.1271/bbb.56.2020. ISSN   0916-8451.
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