10-hydroxy-2-decenoic acid profile

10-hydroxy-2-decenoic acid (10-HDA) is a **fatty acid** produced by **honeybees** (specifically queen bees) that plays a crucial role in **queen bee development and social organization** within a hive.

Here's why it's important for research:

**1. Queen Bee Development and Reproduction:**

* **Royal jelly:** 10-HDA is a key component of royal jelly, the highly nutritious food that worker bees feed to queen larvae.
* **Queen development:** 10-HDA contributes to the development of queen bee characteristics, including larger size, increased ovary development, and a longer lifespan.

**2. Social Organization and Communication:**

* **Queen pheromone:** 10-HDA is part of the queen's pheromone blend, which signals her presence and inhibits worker bees from developing into queens.
* **Colony regulation:** The pheromone helps regulate the colony's social structure and ensures that there is only one queen in the hive.

**3. Research Applications:**

* **Beekeeping:** Understanding 10-HDA can help beekeepers manage their colonies more effectively, for example, by optimizing queen rearing practices.
* **Agriculture:** 10-HDA's role in bee development could be used to improve pollination efficiency in crops.
* **Medicine:** Studies have shown that 10-HDA has potential anti-inflammatory, antimicrobial, and antioxidant properties, making it an area of interest for pharmaceutical research.

**Current Research Focus:**

* **Biosynthesis:** Scientists are investigating the precise mechanisms of 10-HDA production in honeybees.
* **Ecological significance:** Research is exploring the role of 10-HDA in bee colony health and resilience in the face of environmental challenges.
* **Therapeutic potential:** The potential benefits of 10-HDA for human health are being studied, particularly in areas of inflammation and immunity.

In conclusion, 10-HDA is a fascinating molecule that plays a vital role in the social structure and development of honeybee colonies. Ongoing research into its properties and functions has the potential to provide valuable insights into bee biology, improve beekeeping practices, and even lead to new medical treatments.

(E)-10-hydroxydec-2-enoic acid : An omega-hydroxy amino acid that is 2-decenoic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group and in which the C=C double bond has E configuration. It is a component of royal jelly. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	5312738
CHEBI ID	78668
SCHEMBL ID	285440
MeSH ID	M0156353

Synonym
AC-15652
10-hda
nsc87516
nsc-87516
14113-05-4
10-hydroxy-2e-decenoic acid
LMFA01050157
10-hydroxydec-2-enoic acid
n-(2,4,6-trichlorophenoxy)ethyl-n-propylamine
765-01-5
(e)-10-hydroxydec-2-enoic acid
(e)-10-hydroxydec-2-enoic acid;10-hda
A807734
(e)-10-hydroxy-2-decenoic acid
A838726
(e)-10-oxidanyldec-2-enoic acid
AKOS006282270
10-hydroxy-2-decenoic acid ,
queen bee acid
2-decenoic acid, 10-hydroxy-, (e)-
76b519g7tj ,
10-hydroxydecenoic acid
nsc 87516
unii-76b519g7tj
S3827
trans-10-hydroxy-2-decenoic acid
royal jelly acid
10-hydroxydecenoic acid [inci]
10-hydroxy-dec-(e)-2-enoic acid
2-decenoic acid, 10-hydroxy-, (2e)-
10-hydroxy-trans-2-decenoic acid
AKOS025310134
SCHEMBL285440
H1337
(2e)-10-hydroxydec-2-enoic acid
CHEBI:78668
trans-10-hydroxydec-2-enoic acid
(2e)-10-hydroxy-2-decenoic acid #
QHBZHVUGQROELI-SOFGYWHQSA-N
10-hydroxy-2-decylenic acid
AC-34577
mfcd00204506
10h2da
AS-58742
J-007465
CS-0016772
HY-N1363
Z1198152019
10-hydroxy-2-decenoic acid ,(s)
queen bee acid;(e)-10-hydroxy-2-decenoic acid
AS-13924
Q16908844
AMY22616
CCG-266478
10-hydroxy-2(e)-decenoic acid
O10366
A865474
royaljellyacid
DTXSID601045504
EN300-1704333

Role	Description
animal metabolite	Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
geroprotector	Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
alpha,beta-unsaturated monocarboxylic acid	A monocarboxylic acid in which the carbon of the carboxy group is directly attached to a C=C or C#C bond.
straight-chain fatty acid	Any fatty acid whose skeletal carbon atoms form an unbranched open chain.
hydroxy monounsaturated fatty acid	Any monounsaturated fatty acid carrying one or more hydroxy substituents.
omega-hydroxy-medium-chain fatty acid	A omega-hydroxy-fatty acid with a chain length ranging from C6 to C12.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	10 (12.99)	18.7374
1990's	4 (5.19)	18.2507
2000's	8 (10.39)	29.6817
2010's	36 (46.75)	24.3611
2020's	19 (24.68)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	1 (1.25%)	5.53%
Reviews	4 (5.00%)	6.00%
Case Studies	1 (1.25%)	4.05%
Observational	0 (0.00%)	0.25%
Other	74 (92.50%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2	1	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
sebacic acid sebacic acid : An alpha,omega-dicarboxylic acid that is the 1,8-dicarboxy derivative of octane.	2.13	1	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	human metabolite; plant metabolite
uridine [no description available]	2.11	1	uridines	drug metabolite; fundamental metabolite; human metabolite
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	2.05	1
5-fluorouridine [no description available]	2.11	1	organofluorine compound; uridines	mutagen
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.05	1	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
3-hydroxyoctanoic acid 3-hydroxyoctanoic acid : An 8-carbon, beta-hydroxy fatty acid which may be a marker for primary defects of beta-hydroxy fatty acid metabolism. Repeating unit of poly(3-hydroxyoctanoic acid), a biopolymer used by numerous bacterial species as carbon and energy reserves.	2.08	1	3-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; medium-chain fatty acid
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.15	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	2.31	1
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2.05	1	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
10-hydroxycapric acid 10-hydroxycapric acid : A 10-carbon, omega-hydroxy fatty acid, shown to be the preferred hydroxylation product (together with the 9-OH isomer) of capric acid in biosystems, and used as a standard in lipid assays; reported to have cytotoxic effects.	2.83	3	omega-hydroxy-medium-chain fatty acid; straight-chain saturated fatty acid
n-hydroxysuccinimide N-hydroxysuccinimide: structure	2.11	1
4-decenoate 4-decenoic acid: RN given refers to (Z)-isomer; RN for cpd without isomeric designation not available 5/88	2.13	1
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	2.08	1	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2.05	1	cinnamic acid	plant metabolite
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	7.6	1	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
geraniol [no description available]	2.31	1	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	2.03	1
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.05	1	caffeic acid	geroprotector; mouse metabolite
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	2.05	1	cinnamate ester; tannin	food component; plant metabolite
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.13	1
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.03	1
2-decenoic acid 2-decenoic acid: RN given refers to cpd without isomeric designation. decenoic acid : Any C10 monounsaturated fatty acid having a double bond in the carbon backbone.. trans-2-decenoic acid : A 2-decenoic acid having its double bond in the trans configuration. It is an intermediate metabolite in the fatty acid synthesis.. 2-decenoic acid : A decenoic acid having its double bond in position 2.	9.32	6	2-decenoic acid	human metabolite
artepillin c artepillin C: RN refers to (E)-isomer	2.05	1
sincalide Sincalide: An octapeptide hormone present in the intestine and brain. When secreted from the gastric mucosa, it stimulates the release of bile from the gallbladder and digestive enzymes from the pancreas.	2.08	1	oligopeptide
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	2.03	1
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.05	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
baccharin baccharin: antileukemic trichothecene triepoxide isolated from Baccharis megapotamica, a higher plant but may be plant-altered fungal metabolite; structure	2.05	1

Condition	Relationship Strength	Studies
Colitis Gravis [description not available]	2.41	1
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	7.41	1
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	2.41	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.41	1
Alloxan Diabetes [description not available]	2.41	1
Diabetes Mellitus, Adult-Onset [description not available]	2.41	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	2.41	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.59	2
Age-Related Osteoporosis [description not available]	2.25	1
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	2.25	1
Atrophy, Muscle [description not available]	2.25	1
Muscular Atrophy Derangement in size and number of muscle fibers occurring with aging, reduction in blood supply, or following immobilization, prolonged weightlessness, malnutrition, and particularly in denervation.	2.25	1
Sarcopenia Progressive decline in muscle mass due to aging which results in decreased functional capacity of muscles.	2.25	1
Cancer of Lung [description not available]	2.25	1
Lung Neoplasms Tumors or cancer of the LUNG.	2.25	1
Carcinoma, Anaplastic [description not available]	2.31	1
Cancer of Colon [description not available]	2.63	2
Experimental Neoplasms [description not available]	2.31	1
Angiogenesis, Pathologic [description not available]	2.31	1
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.31	1
Colonic Neoplasms Tumors or cancer of the COLON.	2.63	2
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.15	1
Insulin Sensitivity [description not available]	2.15	1
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	7.15	1
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	7.15	1
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	7.15	1
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	2.15	1
Weight Gain Increase in BODY WEIGHT over existing weight.	2.15	1
Adverse Drug Event [description not available]	3.09	1
Benign Neoplasms [description not available]	3.09	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.09	1
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	3.09	1
Allergic Contact Dermatitis [description not available]	2.21	1
Hand Dermatosis [description not available]	2.21	1
Hand Dermatoses Skin diseases involving the HANDS.	2.21	1
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	2.21	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	3.39	2
Rheumatoid Arthritis [description not available]	8.91	4
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	3.91	4
Innate Inflammatory Response [description not available]	2.13	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.13	1
Skin Aging The process of aging due to changes in the structure and elasticity of the skin over time. It may be a part of physiological aging or it may be due to the effects of ultraviolet radiation, usually through exposure to sunlight.	2.06	1
Group A Strep Infection [description not available]	2.07	1
Streptococcal Infections Infections with bacteria of the genus STREPTOCOCCUS.	2.07	1
Hyperlipemia [description not available]	2.01	1
Hyperlipidemias Conditions with excess LIPIDS in the blood.	2.01	1
Experimental Leukemia [description not available]	1.93	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.03	1

10-hydroxy-2-decenoic acid

Description

Cross-References

Synonyms (60)

Research Excerpts

Roles (2)

Drug Classes (4)

Research

Studies (77)

Study Types