(6E)-1,7-Bis(4-hydroxyphenyl)-6-hepten-3-one

(6E)-1,7-Bis(4-hydroxyphenyl)-6-hepten-3-one is a naturally occurring phenolic compound with significant biological potential, first identified and isolated from the rhizomes of Curcuma kwangsiensis. This compound belongs to the class of diarylheptanoids, a family of natural products known for their diverse pharmacological activities, and is characterized by a unique chemical structure consisting of two 4-hydroxyphenyl groups linked by a seven-carbon chain with an enone moiety at the 3-position and a trans double bond at the 6-position (denoted by the "6E" configuration).
With a molecular formula that supports its phenolic nature and a molecular weight of 296.36 , this compound has garnered attention in the scientific community due to its well-documented biological activities. Unlike some of its structural analogues which may have multiple double bonds, (6E)-1,7-Bis(4-hydroxyphenyl)-6-hepten-3-one features a single unsaturation in the heptenyl chain, a structural trait that contributes to its distinct biological profiles.
To date, no widely recognized alternative English names (aliases) for (6E)-1,7-Bis(4-hydroxyphenyl)-6-hepten-3-one have been reported in scientific literature or supplier databases. Its identification is primarily reliant on its systematic IUPAC name and, in research contexts, it is occasionally referenced by numerical designations (e.g., "compound 7") in studies focusing on natural product isolation from Curcuma species.

Naturally Derived Origin: Sourced from the rhizomes of Curcuma kwangsiensis, a plant with a history of use in traditional medicinal practices, ensuring a connection to natural product research frameworks.
Well-Characterized Biological Activity: Exhibits targeted inhibitory effects on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in macrophages, with a defined IC₅₀ value of 8.93 μM , providing quantifiable data for experimental design.
Specific Antimelanogenic Potential: Demonstrates potent activity in regulating melanin production, with an IC₅₀ of 1.24 μM in inhibiting theophylline-induced melanin synthesis in mouse B16-4A5 cells after 72 hours.
Defined Chemical Identity: Possesses a clear molecular weight of 296.36 and a distinct (6E) configuration, enabling precise structural verification and reproducibility in research applications.

Anti-Inflammatory Drug Discovery: Serves as a lead compound or reference standard in studies investigating LPS-induced inflammatory pathways, particularly in macrophage-mediated inflammation, due to its proven ability to inhibit NO production. Researchers use it to explore mechanisms of inflammatory regulation and develop novel anti-inflammatory agents.
Cosmeceutical Research: Applied in studies focused on skin lightening and melanogenesis inhibition. Its low IC₅₀ in B16-4A5 cells makes it a promising candidate for developing ingredients that regulate skin pigmentation and address hyperpigmentation disorders.
Natural Product Pharmacology: Acts as a model compound for investigating the structure-activity relationships (SAR) of diarylheptanoids, helping researchers understand how structural modifications impact biological efficacy in this compound class.
Cellular Signaling Studies: Used to probe pathways related to melanin synthesis (e.g., theophylline-mediated signaling) and inflammatory response (e.g., NF-κB or iNOS pathways), providing insights into cellular regulation mechanisms.

Researchers interested in (6E)-1,7-Bis (4-hydroxyphenyl)-6-hepten-3-one often seek related diarylheptanoids and phenolic compounds with overlapping biological activities. Key examples include (4E,6E)-1,7-bis (4-hydroxyphenyl)-4,6-heptadien-3-one, which exhibits anti-adipogenic activity by inhibiting PPARγ and C/EBPα ; (1E,4E,6E)-1,7-bis (4-hydroxyphenyl)-1,4,6-heptatrien-3-one, a triene analogue with potent anti-adipogenic and inflammatory regulatory effects ; and batatasin I, which modulates adipogenesis via AMPK and CPT-1 pathways. These compounds share structural similarities (diarylheptanoid backbone or phenolic groups) and are widely used in parallel studies of inflammation, pigmentation, and metabolic regulation. If you are interested in related products, you can directly contact us or inquire about product customization services.