A natural metabolite of riboflavin
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Lumichrome

Item No. 20730

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7,8-dimethyl-benzo[g]pteridine-2,4(1H,3H)-dione
CAS Number
1086-80-2
Synonyms
  • 7,8-Dimethylalloxazine
  • NSC 96911
Molecular Formula
C12H10N4O2
Formula Weight
242.2
Purity
≥90%
Formulation
A crystalline solid
λmax
219, 248, 335, 384 nm
SMILES
CC1=C(C)C=C(NC(C2=N3)=NC(NC2=O)=O)C3=C1
InChi Code
InChI=1S/C12H10N4O2/c1-5-3-7-8(4-6(5)2)14-10-9(13-7)11(17)16-12(18)15-10/h3-4H,1-2H3,(H2,14,15,16,17,18)
InChi Key
ZJTJUVIJVLLGSP-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $40

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    250 mg

    $73

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    500 mg

    $96

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    1 g

    $132

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    Product Description

    Lumichrome is a natural metabolite of riboflavin. It can be made by photolysis of riboflavin or it can be produced enzymatically in certain microbes and plants.1,2,3 Lumichrome produced by Rhizobium and other bacterial species induces major developmental changes in plants at nanomolar concentrations.2,4 Lumichrome can stimulate larval metamorphosis in ascidians and activate the LasR quorum sensing receptor of bacteria.5,6 Lumichrome competitively inhibits the uptake of riboflavin by riboflavin transporters from prokaryotes and eukaryotes.7,8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ahmad, I., Anwar, Z., Ahmed, S., et al. Solvent effect on the photolysis of riboflavin. AAPS PharmSciTech. 16(5), 1122-1128 (2015).

    2. Dakora, F.D., Matiru, V.N., and Kanu, A.S. Rhizosphere ecology of lumichrome and riboflavin, two bacterial signal molecules eliciting developmental changes in plants. Front. Plant Sci. 6(700), (2015).

    3. Yamamoto, K., and Asano, Y. Efficient production of lumichrome by Microbacterium sp. strain TPU 3598. Appl. Environ. Microbiol. 81(21), 7360-7367 (2015).

    4. Matiru, V.N., and Dakora, F.D. The rhizosphere signal molecule lumichrome alters seedling development in both legumes and cereals. New Phytol. 166(2), 439-444 (2005).

    5. Rajamani, S., Bauer, W.D., Robinson, J.B., et al. The vitamin riboflavin and its derivative lumichrome activate the LasR bacterial quorum sensing receptor. Mol. Plant Microbe. Interact. 21(9), 1184-1192 (2008).

    6. Tsukamoto, S., Kato, H., Hirota, H., et al. Lumichrome. A larval metamorphosis-inducing substance in the ascidian Hhalocynthia roretzi. Eur. J. Biochem. 264(3), 785-789 (1999).

    7. Balcazar, D.E., Vanrell, M.C., Romano, P.S., et al. The superfamily keeps growing: Identification in trypanosomatids of RibJ, the first riboflavin transporter family in protists. PLoS Negl. Trop. Dis. 11(4), e0005513 (2017).

    8. Said, H.M., Wang, S., and Ma, T.Y. Mechanism of riboflavin uptake by cultured human retinal pigment epithelial ARPE-19 cells: Possible regulation by an intracellular Ca2+-calmodulin-mediated pathway. J. Physiol. 556 (Pt 2), 369-377 (2005).