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HCID 12921作成日：2026年11月3日

2-オクチル-1-シクロプロペン-1-オクタン酸

2-オクチル-1-シクロプロペン-1-オクタン酸 · ステルクル酸 · 8-(2-オクチルシクロプロパ-1-エン-1-イル)オクタン酸 · Sterculinic acid · STERCULIC ACID · 9,10-Methylene-9-octadecenoicacid · 2-Octyl-1-cyclopropene-1-octanoic acid · 8-(2-Octacyclopropen-1-yl)octanoic acid

https://huagongshe.com/ja/chemical/12921

識別子と物理属性

CAS No.	55088-60-3
分子式	C19H34O2
平均分子量	294.5 g/mol
単同位体質量	294.25588032 g/mol
SMILES	CCCCCCCCC1=C(CCCCCCCC(=O)O)C1
InChIKey	PQRKPYLNZGDCFH-UHFFFAOYSA-N
PubChem CID	12921
ChEMBL	CHEMBL3677268
ChEBI	CHEBI:9261
DTXSID	DTXSID90970445
現地名	2-オクチル-1-シクロプロペン-1-オクタン酸

化学・物理的性質

XLogP	5.8
極性表面積	37.3
水素結合供与体数	1
水素結合受容体数	2
回転可能結合数	15
重原子数	21
形式電荷	0
複雑度	318
物質分類	Other Classes -> Organic Acids
脂質	Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Carbocyclic fatty acids [FA0114]
Collision Cross Section	172.7 Å² [M-H]- [CCS Type: TIMSMethod: single field calibrated]
融点	19 °C
沸点	418.7±24.0 °C(Predicted)
密度	0.948±0.06 g/cm3(Predicted)
貯蔵条件	Store at -20°C
溶解度	Chloroform: solubleEther: solubleHexane: solubleMethanol: soluble
外観・状態	A liquid
pKa（酸解離定数）	4.78±0.10(Predicted)
色	Colorless to light yellow

安全性と法規制

有害性の概要	Malvalic and sterculic acid are the primary cyclopropenoid fatty acids (CPRAs) in cottonseed oilThey are synergistic with aflatoxin B1, producing hepatic carcinoma in rainbow trout[HSDB]
Special Reports	THE ROLE OF DIET & NUTRITION IN MODIFYING TUMOR INDUCTION BY CHEMICAL CARCINOGENS IN FOODS & FEEDS IS REVIEWED. FOOD CONTAMINANTS OF MAJOR CONCERN INCLUDE STERCULIC ACID & MALVALIC ACID.[PETERING HGDIET, NUTRITION, AND CANCERADV EXP MED BIOL 91: 207 (1977)]
相互作用	AFLATOXIN Q1 (AFQ), A BIOTRANSFORMATION METABOLITE OF AFLATOXIN B1 (AFB), IS FORMED IN VITRO BY HUMAN & MONKEY LIVER MICROSOMES. AFQ WAS FED TO DUPLICATE LOTS OF 80 RAINBOW TROUT FINGERLINGS @ 100 PPB IN A SEMI-PURIFIED TEST DIET FOR 10 MONTHS. ADDNL LOTS WERE FED 100 PPB AFQ PLUS 50 PPM STERCULIC ACID, & 50 PPM CYCLOPROPENE FATTY ACID (CPFA), 4 PPB AFB & THE BASAL TEST DIET TO SERVE AS CONTROLS. HEPATOCELLULAR CARCINOMA INCIDENCES @ 12 MONTHS WERE AS FOLLOWS: 100 PPB AFQ- 12/114 (10.6%)4 PPB AFB- 55/114 (48.2%)50 PPM CPFA- 44/107 (41.1%)100 PPB AFQ PLUS 50 PPM CPFA (STERCULIC ACID)- 106/119 (89.1%) & CONTROL 0/120 (0%). RESULTS ESTABLISH THE CARCINOGENICITY OF AFQ TO RAINBOW TROUT, THE SYNERGISTIC INTERACTION BETWEEN AFQ & CPFA & INDICATE THAT AFQ IS A POTENT LIVER CARCINOGEN ABOUT 100 TIMES LESS CARCINOGENIC THAN AFB.RAINBOW TROUT FED A DIET CONTAINING 20 UG OCHRATOXIN A PER KG OF DIET, TOGETHER WITH STERCULIC ACID, DEVELOPED HEPATOMAS (NUMBER UNSPECIFIED). NO TUMORS WERE OBSERVED WHEN OCHRATOXIN A WAS FED ALONE AT CONCN OF 16, 32, OR 64 UG/KG OF DIET FOR 8 MONTHS.RAINBOW TROUT FED A DIET CONTAINING 200 PPM OF STERCULIC ACID & MALVALIC ACID, SUBSTANCES THAT GREATLY INCR THE SENSITIVITY OF TROUT LIVER CELLS TO CARCINOGENIC EFFECTS OF AFLATOXIN B1. AFTER 4 WK, PECULIAR CLEFT-LIKE STRIATIONS APPEARED IN CYTOPLASM OF HEPATOCYTES. THESE ALTERATIONS BECAME PROGRESSIVELY MORE FREQUENT & MARKED WITH CONTINUED FEEDING OF DIET. AT 8 & 12 WK, ROUGH-SURFACED ENDOPLASMIC RETICULUM CONTAINED MANY PARALLEL ARRAYS & WHORLED PROFILES OF MEMBRANE MATERIAL. GLUCOSE-6-PHOSPHATASE ACTIVITY IN LIVER WAS SIGNIFICANTLY DECREASED.IN MALE WEANLING RATS FED BASAL DIETS OF SATURATED OR UNSATURATED FAT, THE FOLLOWING ADDITIONS WERE MADE: BASAL DIETAFLATOXIN B1 @ 1.7 PPMSTERCULIC ACID @ 210 PPM& AFLATOXIN B1 @ 1.7 PPM, PLUS STERCULIC ACID @ 210 PPM. RATS CONSUMED THESE DIETS FOR 2 MONTHS & THEREAFTER WERE FED UNSUPPLEMENTED BASAL DIET UNTIL SACRIFICE 9 MONTHS LATER. GROWTH WAS DEPRESSED IN ALL RATS GIVEN DIETARY SUPPLEMENTS BUT NO SYNERGISTIC INHIBITION WAS OBSERVED, REGARDLESS OF FAT SOURCE. LIVER WEIGHT DOUBLED IN RESPONSE TO AFLATOXIN

2-オクチル-1-シクロプロペン-1-オクタン酸

識別子と物理属性

CAS No.

55088-60-3

分子式

C19H34O2

平均分子量

294.5 g/mol

単同位体質量

294.25588032 g/mol

SMILES

CCCCCCCCC1=C(CCCCCCCC(=O)O)C1

InChIKey

PQRKPYLNZGDCFH-UHFFFAOYSA-N

PubChem CID

12921

ChEMBL

CHEMBL3677268

ChEBI

CHEBI:9261

DTXSID

DTXSID90970445

現地名

2-オクチル-1-シクロプロペン-1-オクタン酸

化学・物理的性質

XLogP

5.8

極性表面積

37.3

水素結合供与体数

水素結合受容体数

回転可能結合数

重原子数

形式電荷

複雑度

318

物質分類

Other Classes -> Organic Acids

脂質

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Carbocyclic fatty acids [FA0114]

Collision Cross Section

172.7 Å² [M-H]- [CCS Type: TIMSMethod: single field calibrated]

融点

19 °C

沸点

418.7±24.0 °C(Predicted)

密度

0.948±0.06 g/cm3(Predicted)

貯蔵条件

Store at -20°C

溶解度

Chloroform: solubleEther: solubleHexane: solubleMethanol: soluble

外観・状態

A liquid

pKa（酸解離定数）

4.78±0.10(Predicted)

色

Colorless to light yellow

安全性と法規制

有害性の概要

Malvalic and sterculic acid are the primary cyclopropenoid fatty acids (CPRAs) in cottonseed oilThey are synergistic with aflatoxin B1, producing hepatic carcinoma in rainbow trout[HSDB]

Special Reports

THE ROLE OF DIET & NUTRITION IN MODIFYING TUMOR INDUCTION BY CHEMICAL CARCINOGENS IN FOODS & FEEDS IS REVIEWED. FOOD CONTAMINANTS OF MAJOR CONCERN INCLUDE STERCULIC ACID & MALVALIC ACID.[PETERING HGDIET, NUTRITION, AND CANCERADV EXP MED BIOL 91: 207 (1977)]

相互作用

AFLATOXIN Q1 (AFQ), A BIOTRANSFORMATION METABOLITE OF AFLATOXIN B1 (AFB), IS FORMED IN VITRO BY HUMAN & MONKEY LIVER MICROSOMES. AFQ WAS FED TO DUPLICATE LOTS OF 80 RAINBOW TROUT FINGERLINGS @ 100 PPB IN A SEMI-PURIFIED TEST DIET FOR 10 MONTHS. ADDNL LOTS WERE FED 100 PPB AFQ PLUS 50 PPM STERCULIC ACID, & 50 PPM CYCLOPROPENE FATTY ACID (CPFA), 4 PPB AFB & THE BASAL TEST DIET TO SERVE AS CONTROLS. HEPATOCELLULAR CARCINOMA INCIDENCES @ 12 MONTHS WERE AS FOLLOWS: 100 PPB AFQ- 12/114 (10.6%)4 PPB AFB- 55/114 (48.2%)50 PPM CPFA- 44/107 (41.1%)100 PPB AFQ PLUS 50 PPM CPFA (STERCULIC ACID)- 106/119 (89.1%) & CONTROL 0/120 (0%). RESULTS ESTABLISH THE CARCINOGENICITY OF AFQ TO RAINBOW TROUT, THE SYNERGISTIC INTERACTION BETWEEN AFQ & CPFA & INDICATE THAT AFQ IS A POTENT LIVER CARCINOGEN ABOUT 100 TIMES LESS CARCINOGENIC THAN AFB.RAINBOW TROUT FED A DIET CONTAINING 20 UG OCHRATOXIN A PER KG OF DIET, TOGETHER WITH STERCULIC ACID, DEVELOPED HEPATOMAS (NUMBER UNSPECIFIED). NO TUMORS WERE OBSERVED WHEN OCHRATOXIN A WAS FED ALONE AT CONCN OF 16, 32, OR 64 UG/KG OF DIET FOR 8 MONTHS.RAINBOW TROUT FED A DIET CONTAINING 200 PPM OF STERCULIC ACID & MALVALIC ACID, SUBSTANCES THAT GREATLY INCR THE SENSITIVITY OF TROUT LIVER CELLS TO CARCINOGENIC EFFECTS OF AFLATOXIN B1. AFTER 4 WK, PECULIAR CLEFT-LIKE STRIATIONS APPEARED IN CYTOPLASM OF HEPATOCYTES. THESE ALTERATIONS BECAME PROGRESSIVELY MORE FREQUENT & MARKED WITH CONTINUED FEEDING OF DIET. AT 8 & 12 WK, ROUGH-SURFACED ENDOPLASMIC RETICULUM CONTAINED MANY PARALLEL ARRAYS & WHORLED PROFILES OF MEMBRANE MATERIAL. GLUCOSE-6-PHOSPHATASE ACTIVITY IN LIVER WAS SIGNIFICANTLY DECREASED.IN MALE WEANLING RATS FED BASAL DIETS OF SATURATED OR UNSATURATED FAT, THE FOLLOWING ADDITIONS WERE MADE: BASAL DIETAFLATOXIN B1 @ 1.7 PPMSTERCULIC ACID @ 210 PPM& AFLATOXIN B1 @ 1.7 PPM, PLUS STERCULIC ACID @ 210 PPM. RATS CONSUMED THESE DIETS FOR 2 MONTHS & THEREAFTER WERE FED UNSUPPLEMENTED BASAL DIET UNTIL SACRIFICE 9 MONTHS LATER. GROWTH WAS DEPRESSED IN ALL RATS GIVEN DIETARY SUPPLEMENTS BUT NO SYNERGISTIC INHIBITION WAS OBSERVED, REGARDLESS OF FAT SOURCE. LIVER WEIGHT DOUBLED IN RESPONSE TO AFLATOXIN