hydrangenol CAS 480-47-7

Introduction：Basic information about hydrangenol CAS 480-47-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

hydrangenol Basic information

• Product Name: hydrangenol
• Synonyms: hydrangenol;3-(4-Hydroxyphenyl)-8-hydroxy-3,4-dihydro-1H-2-benzopyran-1-one;3-(4-Hydroxyphenyl)-8-hydroxyisochroman-1-one;3,4-Dihydro-8-hydroxy-3-(4-hydroxyphenyl)-1H-2-benzopyran-1-one;Hydrangel;1H-2-Benzopyran-1-one, 3,4-dihydro-8-hydroxy-3-(4-hydroxyphenyl)-;Hydrangenol, 10 mM in DMSO
• CAS: 480-47-7
• MF: C15H12O4
• MW: 256.25
• EINECS: 200-258-5
• Mol File: 480-47-7.mol

hydrangenol Chemical Properties

• Melting point: 181-182 °C(Solv: ethanol (64-17-5))
• Boiling point: 528.3±50.0 °C(Predicted)
• density: 1.386±0.06 g/cm3(Predicted)
• storage temp.: 2-8°C
• pka: 9.57±0.30(Predicted)
• form: Solid
• color: White to off-white
• Cosmetics Ingredients Functions: SKIN CONDITIONING HAIR CONDITIONING
• LogP: 2.339 (est)

hydrangenol Usage And Synthesis

Description

Hydrangenol is the allergen of so me hydrangeaceae(Hortensia)

Uses

Hydrangenol is an orally active antiphotoaging compound. It can be isolated from Hydrangea serrata leaves. Hydrangenol prevents wrinkle formation by reducing MMP and inflammatory cytokine expression and increasing moisturizing factors and antioxidant genes level[1].

Definition

ChEBI: A member of the class of dihydroisocoumarins that is 3,4-dihydroisocoumarin substituted by a hydroxy group at position 8 and a 4-hydroxyphenyl group at position 3. It has been isolated from the roots of Scorzonera judaica and exhibits anti-allrgic activity.

Contact allergens

Hydrangenol is the allergen of hydrangea (Hydrangeamacrophylla Thunb, Hydrangeaceae family).

Synthesis

Take 500g of dried leaves of Cow White Vine crushed into coarse powder, extracted with water for 2 times, combined with the extract, concentrated under reduced pressure to a density of 1.14 (60 ??), add ethanol to make the concentration of alcohol to 60%, refrigerated at 0 ~ 2 ?? for 24h, filtered, filtrate concentrated under reduced pressure to get the extract; the extract was dissolved in methanol, added to the silica gel mixing samples, dried, and then separated by column chromatography. Gradient elution was carried out by petroleum ether-ethyl acetate system, and the eluates were combined under the reference of thin-layer chromatography, in which the petroleum ether-ethyl acetate (89??11??87??13) section was repeatedly recrystallized by ethanol to obtain the compound hydrangeol (white crystal, 1.0g).

in vivo

Hydrangenol (5-40 mg/kg; p.o.; daily for 7 weeks) mitigated wrinkle formation, dorsal thickness, dehydration, and collagen degradation in UVB-irradiated HR-1 hairless mice^[1].

• Animal Model: UVB-irradiated HR-1 hairless mice^[1]
• Dosage: 5, 10, 20, or 40 mg/kg
• Administration: Oral gavage; daily for 7 weeks
• Result: Increased the expression of involucrin, filaggrin, and aquaporin-3 (AQP3) as well as hyaluronic acid (HA) production via hyaluronidase (HYAL)-1/-2 downregulation. Increased the expression of Pro-COL1A1. Decreased the expression matrix metalloproteinase (MMP)-1/-3, cyclooxygenase-2 (COX-2), and interleukin-6 (IL-6). Attenuated the phosphorylation of mitogen-activated protein kinases (MAPKs) including ERK and p38, activator protein 1 (AP-1) subunit, and signal transduction and activation of transcription 1 (STAT1). Upregulated the expression of nuclear factor-E2-related factor 2 (Nrf2), heme oxygenase-1 (HO-1), NAD(P)H quinone dehydrogenase 1 (NQO-1), glutamate cysteine ligase modifier subunit (GCLM), and glutamate cysteine ligase catalysis subunit (GCLC).

IC 50

MMP-1; MMP-3; COX-2; IL-6

References

[1] Myung DB, et al. Hydrangenol Isolated from the Leaves of Hydrangea serrata Attenuates Wrinkle Formation and Repairs Skin Moisture in UVB-Irradiated Hairless Mice. Nutrients. 2019 Oct 2;11(10):2354. DOI:10.3390/nu11102354