PRODUCTS

E100 (CURCUMIN)

CAS NUMBER: 458-37-7

EC NUMBER: 617-027-4

MOLECULAR FORMULA: C21H20O6

MOLECULAR WEIGHT: 368.4

IUPAC NAME: (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

E100 (Curcumin) is a bright yellow chemical produced by plants of the Curcuma longa species.
E100 (Curcumin) is the principal E100 (Curcumin)oid of turmeric (Curcuma longa), a member of the ginger family, Zingiberaceae.
E100 (Curcumin) is sold as:
-an herbal supplement,
-cosmetics ingredient,
-food flavoring,
-food coloring

Chemically, E100 (Curcumin) is a diarylheptanoid, belonging to the group of E100 (Curcumin)oids, which are phenolic pigments responsible for the yellow color of turmeric.
Laboratory and clinical research have not confirmed any medical use for E100 (Curcumin).
E100 (Curcumin) is difficult to study because it is both unstable and poorly bioavailable.
E100 (Curcumin) is unlikely to produce useful leads for drug development.

History:
E100 (Curcumin) was named in 1815 when Vogel and Pierre Joseph Pelletier reported the first isolation of a "yellow coloring-matter" from the rhizomes of turmeric.
Later, it was found to be a mixture of resin and turmeric oil.
In 1910, Milobedzka and Lampe reported the chemical structure of E100 (Curcumin) to be as diferuloylmethane.
Later in 1913, the same group accomplished the synthesis of the compound.
Although E100 (Curcumin) has been used historically in Ayurvedic medicine, its potential for medicinal properties remains unproven as a therapy when used orally.

USES OF E100 (Curcumin)
E100 (Curcumin) powder:
The most common applications are as an ingredient in dietary supplement, in cosmetics, as flavoring for foods, such as turmeric-flavored beverages in South and Southeast Asia, and as coloring for foods, such as:
-curry powders,
-mustards,
-butters,
-cheeses

As a food additive for orange-yellow coloring in prepared foods, its E number is E 100 in the European Union.
E100 (Curcumin) is also approved by the U.S. FDA to be used as a food coloring in USA.

Chemistry:
A bright red substance in a small glass flask, held by gloved fingers
E100 (Curcumin) becomes bright red when it interacts electrostatically with phospholipid film.
E100 (Curcumin) incorporates a seven carbon linker and three major functional groups: an α,β-unsaturated β-diketone moiety and an aromatic O-methoxy-phenolic group.
The aromatic ring systems, which are phenols, are connected by two α,β-unsaturated carbonyl groups.
E100 (Curcumin) is a diketone tautomer, existing in enolic form in organic solvents and in keto form in water.
The diketones form stable enols and are readily deprotonated to form enolates; the α,β-unsaturated carbonyl group is a good Michael acceptor and undergoes nucleophilic addition.
Because of E100 (Curcumin)'s hydrophobic nature, E100 (Curcumin) is poorly soluble in water.
However, it is easily soluble in organic solvents.
E100 (Curcumin) is used as a complexometric indicator for boron.
E100 (Curcumin) reacts with boric acid to form a red-colored compound, rosocyanine.

Biosynthesis:
The biosynthetic route of E100 (Curcumin) is uncertain.
In 1973, Peter J. Roughley and Donald A. Whiting proposed two mechanisms for E100 (Curcumin) biosynthesis.
The first mechanism involves a chain extension reaction by cinnamic acid and 5 malonyl-CoA molecules that eventually arylize into a E100 (Curcumin)oid.
The second mechanism involves two cinnamate units coupled together by malonyl-CoA.
Both use cinnamic acid as their starting point, which is derived from the amino acid phenylalanine.

Plant biosynthesis starting with cinnamic acid is rare compared to the more common p-coumaric acid.
Only a few identified compounds, such as anigorufone and pinosylvin, build from cinnamic acid.

Stability:
Decontamination of food by ionizing radiation, or food irradiation, is considered a safe and efficient process for elimination of pathogenic bacteria.
Ionizing radiation treatment can be applied to either raw materials or ready to eat foods, with some countries, like the United States, imposing limitations on its use.
In 2016, laboratory research established and compared the radiosensitivity of three organic food colorants including E100 (Curcumin), carmine, and annatto to create data to be used for application whenever food products containing these food colors were to undergo the radiation process.
The researchers used spectrophotometry and capillary electrophoresis to establish radiosensitivity of the three organic food colorants.
Carmine samples were quite stable against radiation treatment, annatto showed limited stability, and E100 (Curcumin) was found to be stable at high temperatures and in acids, but unstable in alkaline conditions and in the presence of light.

What is E100 (Curcumin)?
E100 (Curcumin) is a yellow pigment found primarily in turmeric, a flowering plant of the ginger family best known as a spice used in curry.
E100 (Curcumin)’s a polyphenol with anti-inflammatory properties and the ability to increase the amount of antioxidants that the body produces.

E100 (Curcumin) and the E100 (Curcumin)oids found in turmeric can be extracted to produce supplements that have a much higher potency than turmeric.
However, E100 (Curcumin) is absorbed poorly during digestion, so a myriad of different formulations have been created to improve its bioavailability.
E100 (Curcumin) is the main active ingredient in turmeric.
E100 (Curcumin) has powerful anti-inflammatory effects and is a very strong antioxidant.

What are E100 (Curcumin)’s benefits?
Supplementation of E100 (Curcumin) reliably reduces markers of inflammation and increases the levels of endogenous antioxidants in the body.
More research is needed for many areas of health, but what research there is supports a small to moderate improvement in the symptoms of depression and anxiety, and pain and function in osteoarthritis.
A reduction in LDL-cholesterol, blood glucose and blood pressure is possible, but the research is less consistent and more is needed.

What is the difference between turmeric and E100 (Curcumin)?
E100 (Curcumin) is a popular root/spice, and E100 (Curcumin) is a highly potent chemical in turmeric, but hardly the only one.
E100 (Curcumin) and the E100 (Curcumin)oids are present in turmeric at around 22.21-40.36mg/g in the rhizomes and 1.94mg/g in the tuberous roots, so turmeric is less potent as a source of E100 (Curcumin) than an extract and anti-inflammatory.
However, some studies suggest that turmeric has benefits, and it's possible that it has benefits that E100 (Curcumin) alone doesn't, but more research on this is needed.

E100 (Curcumin), a substance in turmeric, may help to reduce inflammation.
Several studies suggest that it might ease symptoms of osteoarthritis and rheumatoid arthritis, like pain and inflammation.
Other compounds in turmeric might also be medicinal.

E100 (Curcumin) is a component of the Indian spice turmeric (E100 (Curcumin) longa), a type of ginger. E100 (Curcumin) is one of three E100 (Curcumin)oids present in turmeric, the other two being desmethoxyE100 (Curcumin) and bis-desmethoxyE100 (Curcumin).
These E100 (Curcumin)oids give turmeric its yellow color and E100 (Curcumin) is used as a yellow food colorant and food additive.
E100 (Curcumin) is obtained from the dried rhizome of the turmeric plant, which is a perennial herb that is cultivated extensively in south and southeast Asia.
The rhizome or the root is processed to form turmeric which contains 2% to 5% E100 (Curcumin).

E100 (Curcumin) is present in two tautomeric forms known as keto and enol.
The enol form is the more stable in both solid and solution phases.
E100 (Curcumin) can also be used for the quantification of boron since it reacts with boric acid to form a red colored compound called rosocyanine.

E100 (Curcumin) has been the subject of much interest and research over the last few decades due to its medicinal properties.
Research has demonstrated that E100 (Curcumin) is a potent anti-inflammatory agent that can reduce inflammation and may even play a role in cancer treatment.
E100 (Curcumin) has been shown to reduce the transformation, proliferation and spread of tumors and it achieves this through regulation of transcription factors, inflammatory cytokines, growth factors, protein kinases and other enzymes.
E100 (Curcumin) prevents proliferation by interrupting the cell cycle and inducing programmed cell death.
Furthermore, E100 (Curcumin) can inhibit the activation of carcinogens through suppression of certain cytochrome P450 isozymes.

E100 (Curcumin) is a nutritional compound located within the rhizome, or rootstalk, of the turmeric plant.
E100 (Curcumin) is a natural antioxidant that has anti-inflammatory benefits, as well as [possible] benefits related to slowing the aging process and preventing Alzheimer's disease and, potentially, depression

E100 (Curcumin) is a beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups.
E100 (Curcumin) is a natural dyestuff found in the root of Curcuma longa.
E100 (Curcumin) has a role as:
-a metabolite,
-an anti-inflammatory agent,
-an antineoplastic agent,
-a hepatoprotective agent,
-a flavouring agent,
-a biological pigment,
-a nutraceutical,
-an antifungal agent,
-a dye,
-a lipoxygenase inhibitor,
-a ligand,
-a radical scavenger,
-a contraceptive drug,
-an EC 3.5.1.98 (histone deacetylase) inhibitor,
-an immunomodulator,
-an iron chelator,
-a neuroprotective agent,
-a food colouring,
-an EC 1.1.1.21 (aldehyde reductase) inhibitor,
-an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor,
-an EC 1.1.1.205 (IMP dehydrogenase) inhibitor,
-an EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor,
-an EC 1.8.1.9 (thioredoxin reductase) inhibitor,
-an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
-a geroprotector.

E100 (Curcumin) is a polyphenol, a beta-diketone, an enone, a diarylheptanoid and an aromatic ether.
E100 (Curcumin) derives from a ferulic acid.

E100 (Curcumin) is a phytopolylphenol pigment isolated from the plant Curcuma longa, commonly known as turmeric, with a variety of pharmacologic properties.
E100 (Curcumin) blocks the formation of reactive-oxygen species, possesses anti-inflammatory properties as a result of inhibition of cyclooxygenases (COX) and other enzymes involved in inflammation; and disrupts cell signal transduction by various mechanisms including inhibition of protein kinase C.
These effects may play a role in the agent's observed antineoplastic properties, which include inhibition of tumor cell proliferation and suppression of chemically induced carcinogenesis and tumor growth in animal models of cancer.
E100 (Curcumin) appears as orange-yellow needles.

EU Food Additive Definition:
E100 (Curcumin) is obtained by solvent extraction of turmeric i.e. the ground rhizomes of strains ofCurcuma longaL.
In order to obtain a concentrated E100 (Curcumin) powder, the extract is purified by crystallization.
The product consists essentially of E100 (Curcumin)s; i.e. the colouring principle (1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-dien-3,5-dione) and its two desmethoxy derivatives in varying proportions.
Minor amounts of oils and resins naturally occurring in turmeric may be present.

E100 (Curcumin) is also used as the aluminium lake; the aluminium content is less than 30 %.; Only the following solvents may be used in the extraction:
-ethylacetate
-acetone
-carbon dioxide
-dichloromethane
-n-butanol
-methanol
-ethanol
-hexane
-propan-2-ol

Metabolism:
Initially, E100 (Curcumin) undergoes rapid intestinal metabolism to form E100 (Curcumin) glucuronide and E100 (Curcumin) sulfate via O-conjugation.
Other metabolites formed include tetrahydroE100 (Curcumin), hexahydroE100 (Curcumin), and hexahydroE100 (Curcumin)ol via reduction. E100 (Curcumin) may also undergo intensive second metabolism in the liver where the major metabolites were glucuronides of tetrahydroE100 (Curcumin) and hexahydroE100 (Curcumin), with dihydroferulic acid and traces of ferulic acid as further metabolites.
Hepatic metabolites are expected to be excreted in the bile.
Certain E100 (Curcumin) metabolites, such as tetrahydroE100 (Curcumin), retain anti-inflammatory and antioxidant properties.
E100 (Curcumin) has known human metabolites that include E100 (Curcumin) 4-O-glucuronide and O-demethyl E100 (Curcumin).

Mechanism of Action:
E100 (Curcumin) acts as a scavenger of oxygen species, such as hydroxyl radical, superoxide anion, and singlet oxygen and inhibit lipid peroxidation as well as peroxide-induced DNA damage.
E100 (Curcumin) mediates potent anti-inflammatory agent and anti-carcinogenic actions via modulating various signalling molecules.
E100 (Curcumin) suppresses a number of key elements in cellular signal transduction pathways pertinent to growth, differentiation, and malignant transformation; it was demonstrated _in vitro_ that E100 (Curcumin) inhibits protein kinases, c-Jun/AP-1 activation, prostaglandin biosynthesis, and the activity and expression of the enzyme cyclooxygenase (COX)-2.

E100 (Curcumin), a polyphenolic natural product, exhibits therapeutic activity against a number of diseases, attributed mainly to its chemical structure and unique physical, chemical, and biological properties. It is a diferuloyl methane molecule [1,7-bis (4-hydroxy-3- methoxyphenyl)-1,6-heptadiene-3,5-dione)] containing two ferulic acid residues joined by a methylene bridge.
E100 (Curcumin) has three important functionalities: an aromatic o-methoxy phenolic group, alpha, beta-unsaturated beta-diketo moiety and a seven carbon linker. Extensive research in the last two decades has provided evidence for the role of these different functional groups in its crucial biological activities.
A few highlights of chemical structural features associated with the biological activity of E100 (Curcumin) are:
The o-methoxyphenol group and methylenic hydrogen are responsible for the antioxidant activity of E100 (Curcumin), and E100 (Curcumin) donates an electron/ hydrogen atom to reactive oxygen species.
E100 (Curcumin) interacts with a number of biomolecules through non-covalent and covalent binding.
The hydrogen bonding and hydrophobicity of E100 (Curcumin), arising from the aromatic and tautomeric structures along with the flexibility of the linker group are responsible for the non-covalent interactions.
The alpha, beta-unsaturated beta-diketone moiety covalently interacts with protein thiols, through Michael reaction.
The beta-diketo group forms chelates with transition metals, thereby reducing the metal induced toxicity and some of the metal complexes exhibit improved antioxidant activity as enzyme mimics.
New analogues with improved activity are being developed with modifications on specific functional groups of E100 (Curcumin).

E100 (Curcumin) has many pharmaceutical applications, many of which arise from its potent antioxidant properties.
The present research examined the antioxidant activities of E100 (Curcumin) in polar solvents by a comparative study using ESR, reduction of ferric iron in aqueous medium and intracellular ROS/toxicity assays.
ESR data indicated that the steric hindrance among adjacent big size groups within a galvinoxyl molecule limited the E100 (Curcumin) to scavenge galvinoxyl radicals effectively, while E100 (Curcumin) showed a powerful capacity for scavenging intracellular smaller oxidative molecules such as H2O2, HO-, ROO-.
Cell viability and ROS assays demonstrated that E100 (Curcumin) was able to penetrate into the polar medium inside the cells and to protect them against the highly toxic and lethal effects of cumene hydroperoxide.
E100 (Curcumin) also showed good electron-transfer capability, with greater activity than trolox in aqueous solution.
E100 (Curcumin) can readily transfer electron or easily donate H-atom from two phenolic sites to scavenge free radicals.
The excellent electron transfer capability of E100 (Curcumin) is because of its unique structure and different functional groups, including a beta-diketone and several pi electrons that have the capacity to conjugate between two phenyl rings.
Therefore, since E100 (Curcumin) is inherently a lipophilic compound, because of its superb intracellular ROS scavenging activity, it can be used as an effective antioxidant for ROS protection within the polar cytoplasm.

Use and Manufacturing:
E100 (Curcumin) is a natural polyphenol product derived from the rhizome of the Curcuma longa.

In vivo and in vitro studies have uncovered many important bioactivities of E100 (Curcumin), such as:
-antioxidant activity
-inducing cell apoptosis
-inhibiting cell proliferation
-anti-cell adhesion and motility
-anti-angiogenesis
-anti-microbe properties

Based on these functions, E100 (Curcumin) has been used in clinical trials on various inflammatory diseases and cancers.
In the future, it will be necessary to focus attention partly on the clinical application of E100 (Curcumin) in neurodegenerative diseases, cardiovascular diseases and diabetes, because many experiments have clarified the potential value of E100 (Curcumin) in these areas.

The main source of E100 (Curcumin) is the root of Zingiberaceae Curcuma aromatica, rhizome of Curcuma longa (Jiang Huang), Curcuma zedoaria, and Acorus calamus.
Among them, Jiang Huang contains about 3–6% E100 (Curcumin).
The traditional Chinese medicine, Jiang Huang, is the root tuber of perennial herbaceous plant Curcuma longa L. of family Zingiberaceae.
E100 (Curcumin) was firstly recorded in the “Tang materia medica” (Xin Xiu Ben Cao).
E100 (Curcumin) is pungent, bitter, and warm and enters the liver and spleen meridians.
E100 (Curcumin) activates the blood, moves qi, dredges meridians, and alleviates pain.
In India and other Asian countries, Jiang Huang has more than 6000?years of application history.
In Japan, Jiang Huang has a long history of health care, and the people of Okinawa Island regarded Jiang Huang as a holy tribute to the emperor.
Jiang Huang mainly comes from Taiwan, Fujian, Guangdong, Guangxi, Yunnan, and Tibet of China and other regions in East Asia and Southeast Asia.
E100 (Curcumin) grows in warm and humid climate and sunny environment with abundant rainfall and fears cold frost, drought, and flood.
At present, Chinese Pharmacopoeia only included Jiang Huang and Yu Jin which contains E100 (Curcumin), while E100 (Curcumin) is not included.

E100 (Curcumin) is the major yellow pigment in turmeric and curry and has antioxidant, anti-inflammatory, and antitumor activities.
E100 (Curcumin) inhibits nitric oxide (NO) production (IC50 = 6 μM) and reduces inducible nitric oxide synthase (iNOS) activity in LPS-stimulated RAW 264.7 cells.
E100 (Curcumin) inhibits release of histamine and the inflammatory cytokines TNF-α, IL-1β, IL-6, and IL-8 from HMC-1 mast cells.
In vivo, E100 (Curcumin) decreases serum levels of histamine and TNF-α, inhibits histopathological changes of nasal mucosa, and decreases the number of sneezes and nasal rubbing in a mouse model of ovalbumin-induced rhinitis.
E100 (Curcumin) (100 or 200 mg/kg) prevents ovalbumin-induced accumulation of 3-nitrotyrosine (3-NT), a marker of oxidative stress, in mouse heart.
Topical administration of E100 (Curcumin) (1-10 μmol) reduces the number of tumors induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in mouse skin.
Dietary administration of E100 (Curcumin) reduces the number of tongue neoplasms and preneoplastic lesions induced by 4-nitroquinoline 1-oxide (4-NQO) in rats.

E100 (Curcumin) is a bright yellow chemical produced by plants of the Curcuma longa species. It is the principal E100 (Curcumin)oid of turmeric (Curcuma longa), a member of the ginger family, Zingiberaceae.
E100 (Curcumin) is sold as an herbal supplement, cosmetics ingredient, food flavoring, and food coloring.Chemically, E100 (Curcumin) is a diarylheptanoid, belonging to the group of E100 (Curcumin)oids, which are phenolic pigments responsible for the yellow color of turmeric.
Laboratory and clinical research have not confirmed any medical use for E100 (Curcumin).
E100 (Curcumin) is difficult to study because it is both unstable and poorly bioavailable.
E100 (Curcumin) is unlikely to produce useful leads for drug development.

PHYSICAL PROPERTIES OF E100 (Curcumin):

-Molecular Weight: 368.4

-Exact Mass: 368.12598835

-Monoisotopic Mass: 368.12598835

-Topological Polar Surface Area: 93.1 Å²

-Physical Description: E100 (Curcumin) appears as orange-yellow needles

-Color: Orange-yellow

-Form: crystal powder

-Melting Point: 183.0 °C

-Solubility: Insoluble in cold water

-Density: 0.9348 at 59 °F

-Vapor Pressure: 3.08X10-12 mm Hg

-log Kow: 3.29

-Henry's Law constant: 7.04X10-22 atm-cu m/mol

-Stability/Shelf Life: Stable under recommended storage conditions.

-Decomposition: Hazardous decomposition products formed under fire conditions.

-Refractive Index: 1.5118

-Collision Cross Section: 201.6 Å²

E100 (Curcumin) is a bright yellow chemical produced by plants of the Curcuma longa species.
E100 (Curcumin) is the principal E100 (Curcumin)oid of turmeric (Curcuma longa), a member of the ginger family, Zingiberaceae.
Chemically, E100 (Curcumin) is a diarylheptanoid, belonging to the group of E100 (Curcumin)oids, which are phenolic pigments responsible for the yellow color of turmeric.

Laboratory and clinical research have not confirmed any medical use for E100 (Curcumin).
E100 (Curcumin) is difficult to study because it is both unstable and poorly bioavailable.
E100 (Curcumin) is unlikely to produce useful leads for drug development.
E100 (Curcumin) is a yellow pigment found primarily in turmeric, a flowering plant of the ginger family best known as a spice used in curry.

E100 (Curcumin)’s a polyphenol with anti-inflammatory properties and the ability to increase the amount of antioxidants that the body produces.
E100 (Curcumin) is present in two tautomeric forms known as keto and enol.
The enol form is the more stable in both solid and solution phases.
E100 (Curcumin) can also be used for the quantification of boron since it reacts with boric acid to form a red colored compound called rosocyanine.

CHEMICAL PROPERTIES OF E100 (Curcumin):

-Heavy Atom Count: 27

-Formal Charge: 0

-Complexity: 507

-Isotope Atom Count: 0

-Defined Atom Stereocenter Count: 0

-Undefined Atom Stereocenter Count: 0

-Defined Bond Stereocenter Count: 2

-Undefined Bond Stereocenter Count: 0

-Covalently-Bonded Unit Count: 1

-Compound Is Canonicalized: Yes

-XLogP3-AA: 3.2

-Hydrogen Bond Donor Count: 2

-Hydrogen Bond Acceptor Count: 6

-Rotatable Bond Count: 8

SYNONYMS:

E100 (Curcumin)
Diferuloylmethane
Natural yellow 3
Turmeric yellow
Turmeric
Indian saffron
Curcuma
Kacha haldi
Gelbwurz
E100 (Curcumin) I
Souchet
Haidr
Halad
Haldar
Halud
(1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
Merita earth
Terra Merita
Yellow Ginger
Yellow Root
Safran d'Inde
Yo-Kin
Curcuma oil
Golden seal
Orange Root
C.I. Natural Yellow 3
E100 (Curcumin)e
Hydrastis
Indian turmeric
Yellow puccoon
Diferaloylmethane
Turmeric oleoresin
Kurkumin [Czech]
Tumeric yellow
CI Natural Yellow 3
Zlut prirodni 3 [Czech]
Cucurmin
Tumeric oleoresin
1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
Turmeric oleoresin (79%-85% E100 (Curcumin))
Turmeric extract
Oils, curcuma
1,9-Bis(4-hydroxy-3-methoxyphenyl)-2,7-nonadiene-4,6-dione
(1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxy-3-methoxyphenyl)-, (E,E)-
1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxy-3-methoxyphenyl)-, (1E,6E)-
1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
Turmeric oil
Oil of turmeric
(E,E)-1,7-bis(4-Hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
Kurkumin
(1E,6E)-1,7-bis(4-hydroxy-3-methoxy-phenyl)hepta-1,6-diene-3,5-dione
(1E,6E)-1,7-bis[4-hydroxy-3-(methyloxy)phenyl]hepta-1,6-diene-3,5-dione
Zlut prirodni 3
Turmeric, oleoresin
Curcuma oil (Curcuma longa)
Turmeric oil (Curcuma longa L.)
1,5-Di(vanillyliden)acetylaceton
1,5-Divanillyliden-2,4-pentandion
diferuloylmethan
E100 (Curcumin) solution
Haldar, Souchet
Turmeric; Curcuma
2,7-Nonadiene-4,6-dione, 1,9-bis(4-hydroxy-3-methoxyphenyl)-
1,3-Di(3-methoxy-4-hydroxystyryl)propanedial
1,5-dione, 1,7-bis(4-hydroxy-3-methoxyphenyl)-
1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadien-3,5-dione
1,7-bis(4-hydroxy-3-methoxyphenyl)1,6-heptadiene-3,5-dione
1,7-Bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,6-diene-3,5-dione
1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
((E,E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione)
(1E,6E)-1,7-bis(3-methoxy-4-oxidanyl-phenyl)hepta-1,6-diene-3,5-dione
(1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione #
(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione.
(1E,6E)-1,7-Bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,6-diene-3,5-dione
(1Z,6E)-1,7-Bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,6-diene-3,5-dione
1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, (E,E)-
5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,4,6-heptatrien-3-one
5-Hydroxy-1,7-bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,4,6-trien-3-one
1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
(1E,4Z,6E)-5-Hydroxy-1,7-bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,4,6-trien-3-one
(E,E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione (Synthetic)